Čeković, Živorad

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  • Čeković, Živorad (23)
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Author's Bibliography

Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid

Ferjančić, Zorana; Matović, Radomir; Čeković, Živorad; Jiang, Yi; Snyder, James P.; Trajković, Vladimir S.; Saičić, Radomir

(Pergamon-Elsevier Science Ltd, Oxford, 2006)

TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Matović, Radomir
AU  - Čeković, Živorad
AU  - Jiang, Yi
AU  - Snyder, James P.
AU  - Trajković, Vladimir S.
AU  - Saičić, Radomir
PY  - 2006
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/798
AB  - A C,D-seco-paclitaxel derivative 26 was prepared from taxine and tested for biological activity. Chemical reactivity of the seco-compounds proved to be substantially modified, with respects to taxoids. The corresponding C,D-seco-taxoid does not show tubulin stabilizing activity or cytotoxicity. Explanation of these observations based on molecular modeling is provided. (c) 2006 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid
VL  - 62
IS  - 36
SP  - 8503
EP  - 8514
DO  - 10.1016/j.tet.2006.06.080
ER  - 
@article{
author = "Ferjančić, Zorana and Matović, Radomir and Čeković, Živorad and Jiang, Yi and Snyder, James P. and Trajković, Vladimir S. and Saičić, Radomir",
year = "2006",
abstract = "A C,D-seco-paclitaxel derivative 26 was prepared from taxine and tested for biological activity. Chemical reactivity of the seco-compounds proved to be substantially modified, with respects to taxoids. The corresponding C,D-seco-taxoid does not show tubulin stabilizing activity or cytotoxicity. Explanation of these observations based on molecular modeling is provided. (c) 2006 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid",
volume = "62",
number = "36",
pages = "8503-8514",
doi = "10.1016/j.tet.2006.06.080"
}
Ferjančić, Z., Matović, R., Čeković, Ž., Jiang, Y., Snyder, J. P., Trajković, V. S.,& Saičić, R.. (2006). Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid. in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 62(36), 8503-8514.
https://doi.org/10.1016/j.tet.2006.06.080
Ferjančić Z, Matović R, Čeković Ž, Jiang Y, Snyder JP, Trajković VS, Saičić R. Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid. in Tetrahedron. 2006;62(36):8503-8514.
doi:10.1016/j.tet.2006.06.080 .
Ferjančić, Zorana, Matović, Radomir, Čeković, Živorad, Jiang, Yi, Snyder, James P., Trajković, Vladimir S., Saičić, Radomir, "Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid" in Tetrahedron, 62, no. 36 (2006):8503-8514,
https://doi.org/10.1016/j.tet.2006.06.080 . .
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Reactions of alpha-4(20)-epoxy-5-O-mesyltriacetyltaxicine I induced by BF3 center dot Et2O/Bu4NBr

Ferjančić, Zorana; Matović, Radomir; Čeković, Živorad; Saičić, Radomir

(Serbian Chemical Soc, Belgrade, 2006)

TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Matović, Radomir
AU  - Čeković, Živorad
AU  - Saičić, Radomir
PY  - 2006
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/811
AB  - The reaction of alpha-4(20)-epoxy-5-O-mesyltriacetyltaxicin I (2) with (BF3Et2O)-Et-./Bu4NBr can give rise to 4 different products. Each of these products can be obtained selectively, under the appropriate reaction conditions.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Reactions of alpha-4(20)-epoxy-5-O-mesyltriacetyltaxicine I induced by BF3 center dot Et2O/Bu4NBr
VL  - 71
IS  - 7
SP  - 705
EP  - 711
DO  - 10.2298/JSC0607705F
ER  - 
@article{
author = "Ferjančić, Zorana and Matović, Radomir and Čeković, Živorad and Saičić, Radomir",
year = "2006",
abstract = "The reaction of alpha-4(20)-epoxy-5-O-mesyltriacetyltaxicin I (2) with (BF3Et2O)-Et-./Bu4NBr can give rise to 4 different products. Each of these products can be obtained selectively, under the appropriate reaction conditions.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Reactions of alpha-4(20)-epoxy-5-O-mesyltriacetyltaxicine I induced by BF3 center dot Et2O/Bu4NBr",
volume = "71",
number = "7",
pages = "705-711",
doi = "10.2298/JSC0607705F"
}
Ferjančić, Z., Matović, R., Čeković, Ž.,& Saičić, R.. (2006). Reactions of alpha-4(20)-epoxy-5-O-mesyltriacetyltaxicine I induced by BF3 center dot Et2O/Bu4NBr. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 71(7), 705-711.
https://doi.org/10.2298/JSC0607705F
Ferjančić Z, Matović R, Čeković Ž, Saičić R. Reactions of alpha-4(20)-epoxy-5-O-mesyltriacetyltaxicine I induced by BF3 center dot Et2O/Bu4NBr. in Journal of the Serbian Chemical Society. 2006;71(7):705-711.
doi:10.2298/JSC0607705F .
Ferjančić, Zorana, Matović, Radomir, Čeković, Živorad, Saičić, Radomir, "Reactions of alpha-4(20)-epoxy-5-O-mesyltriacetyltaxicine I induced by BF3 center dot Et2O/Bu4NBr" in Journal of the Serbian Chemical Society, 71, no. 7 (2006):705-711,
https://doi.org/10.2298/JSC0607705F . .
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Synthesis, biological evaluation, and modeling of a C,D-seco-taxoid

Ferjančić, Zorana; Matović, Radomir; Čeković, Živorad; Snyder, JP; Saičić, Radomir

(Pergamon-Elsevier Science Ltd, Oxford, 2005)

TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Matović, Radomir
AU  - Čeković, Živorad
AU  - Snyder, JP
AU  - Saičić, Radomir
PY  - 2005
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/716
AB  - A C,D-seco-paclitaxel derivative 12 was prepared and tested for biological activity. The key step in the synthesis was a free radical fragmentation of the bicyclic tertiary alcohol 7 under the conditions of the hypobromite reaction. The compound 12 showed no activity in the tubulin test. (c) 2005 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron Letters
T1  - Synthesis, biological evaluation, and modeling of a C,D-seco-taxoid
VL  - 46
IS  - 30
SP  - 5049
EP  - 5052
DO  - 10.1016/j.tetlet.2005.05.071
ER  - 
@article{
author = "Ferjančić, Zorana and Matović, Radomir and Čeković, Živorad and Snyder, JP and Saičić, Radomir",
year = "2005",
abstract = "A C,D-seco-paclitaxel derivative 12 was prepared and tested for biological activity. The key step in the synthesis was a free radical fragmentation of the bicyclic tertiary alcohol 7 under the conditions of the hypobromite reaction. The compound 12 showed no activity in the tubulin test. (c) 2005 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron Letters",
title = "Synthesis, biological evaluation, and modeling of a C,D-seco-taxoid",
volume = "46",
number = "30",
pages = "5049-5052",
doi = "10.1016/j.tetlet.2005.05.071"
}
Ferjančić, Z., Matović, R., Čeković, Ž., Snyder, J.,& Saičić, R.. (2005). Synthesis, biological evaluation, and modeling of a C,D-seco-taxoid. in Tetrahedron Letters
Pergamon-Elsevier Science Ltd, Oxford., 46(30), 5049-5052.
https://doi.org/10.1016/j.tetlet.2005.05.071
Ferjančić Z, Matović R, Čeković Ž, Snyder J, Saičić R. Synthesis, biological evaluation, and modeling of a C,D-seco-taxoid. in Tetrahedron Letters. 2005;46(30):5049-5052.
doi:10.1016/j.tetlet.2005.05.071 .
Ferjančić, Zorana, Matović, Radomir, Čeković, Živorad, Snyder, JP, Saičić, Radomir, "Synthesis, biological evaluation, and modeling of a C,D-seco-taxoid" in Tetrahedron Letters, 46, no. 30 (2005):5049-5052,
https://doi.org/10.1016/j.tetlet.2005.05.071 . .
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Phenylsulfenylation of nonactivated d-Carbon atom by photolysis of alkyl benzenesulfenates: preparation of 2-phenylthio-5-heptanol (Heptane, 2-phenylthio-5-hydroxy)

Petrović, G.; Saičić, Radomir; Čeković, Živorad; Li, F.; Miller, M.J.

(2005)

TY  - JOUR
AU  - Petrović, G.
AU  - Saičić, Radomir
AU  - Čeković, Živorad
AU  - Li, F.
AU  - Miller, M.J.
PY  - 2005
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/122
T2  - Organic Syntheses
T1  - Phenylsulfenylation of nonactivated d-Carbon atom by photolysis of alkyl benzenesulfenates: preparation of 2-phenylthio-5-heptanol (Heptane, 2-phenylthio-5-hydroxy)
VL  - 81
SP  - 244
EP  - 253
DO  - 10.15227/orgsyn.081.0244
ER  - 
@article{
author = "Petrović, G. and Saičić, Radomir and Čeković, Živorad and Li, F. and Miller, M.J.",
year = "2005",
journal = "Organic Syntheses",
title = "Phenylsulfenylation of nonactivated d-Carbon atom by photolysis of alkyl benzenesulfenates: preparation of 2-phenylthio-5-heptanol (Heptane, 2-phenylthio-5-hydroxy)",
volume = "81",
pages = "244-253",
doi = "10.15227/orgsyn.081.0244"
}
Petrović, G., Saičić, R., Čeković, Ž., Li, F.,& Miller, M.J.. (2005). Phenylsulfenylation of nonactivated d-Carbon atom by photolysis of alkyl benzenesulfenates: preparation of 2-phenylthio-5-heptanol (Heptane, 2-phenylthio-5-hydroxy). in Organic Syntheses, 81, 244-253.
https://doi.org/10.15227/orgsyn.081.0244
Petrović G, Saičić R, Čeković Ž, Li F, Miller M. Phenylsulfenylation of nonactivated d-Carbon atom by photolysis of alkyl benzenesulfenates: preparation of 2-phenylthio-5-heptanol (Heptane, 2-phenylthio-5-hydroxy). in Organic Syntheses. 2005;81:244-253.
doi:10.15227/orgsyn.081.0244 .
Petrović, G., Saičić, Radomir, Čeković, Živorad, Li, F., Miller, M.J., "Phenylsulfenylation of nonactivated d-Carbon atom by photolysis of alkyl benzenesulfenates: preparation of 2-phenylthio-5-heptanol (Heptane, 2-phenylthio-5-hydroxy)" in Organic Syntheses, 81 (2005):244-253,
https://doi.org/10.15227/orgsyn.081.0244 . .
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Stereoselective free radical phenylsulfenylation of a nonactivated delta-carbon atom

Petrović, G.; Saičić, Radomir; Došen-Mićović, Ljiljana; Čeković, Živorad

(Serbian Chemical Soc, Belgrade, 2004)

TY  - JOUR
AU  - Petrović, G.
AU  - Saičić, Radomir
AU  - Došen-Mićović, Ljiljana
AU  - Čeković, Živorad
PY  - 2004
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/668
AB  - A stereoselective free radical introduction of a phenylthio group onto a nonactivated methyl group in the 8-position, adjacent to a prochiral carbon atom, was achieved by photolysis of (-)-menthyl benzenesulfenate in the presence of hexabutylditin and (1R, 3R, 4S, 8S)-9-phenylthiomenthot (4) was obtained with 91 % optical purity. High stereoselectivity of the reaction was calculated (ab initio MP2/6-3 1G**) to be the consequence of the difference in the transition state eneregies (DeltaDeltaG(#) = 5.08 kJ/mol) favouring 4 relative to (1R,3R,4S,8R)-9-phenylthiomenthoI (5). The absolute configuration of a the new chiral carbon atom was confirmed by its correlation with the corresponding menthane-3,9-diol of known stereochemistry.
AB  - Fotolizom (–)-mentil-benzensulfenata u prisustvu heksabutil-dikalaja izvršeno je stereoselektivno uvođenje feniltio grupe na neaktiviranu metil grupu u δ-položaju koja je susedna prohiralnom ugljenikovom atomu i dobiven je (1R 3R, 4S, 8S)-9-feniltio-mentol (4) sa 91 % optičke čistoće. Visoka stereoselektivnost reakcije, potvrđena računom (ab initio MP2/6-21G**) posledica je razlike u energijama prelaznih stanja ΔΔG# = 5.08 kJ/mol) koja favorizuje nastajanje 4 u odnosu na (1R, 3R, 4S, 8R)-9-feniltio-mentol (5). Apsolutna konfiguracija novog hiralnog ugljenikovog atoma potvrđena je korelacijom s odgovarajućim mentan-3,9-diolom poznate stereohemije.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Stereoselective free radical phenylsulfenylation of a nonactivated delta-carbon atom
T1  - Stereoselektivno slobodnoradikalsko fenilsulfenilovanje neaktiviranog δ-ugljenikovog atoma
VL  - 69
IS  - 10
SP  - 737
EP  - 747
DO  - 10.2298/JSC0410737P
ER  - 
@article{
author = "Petrović, G. and Saičić, Radomir and Došen-Mićović, Ljiljana and Čeković, Živorad",
year = "2004",
abstract = "A stereoselective free radical introduction of a phenylthio group onto a nonactivated methyl group in the 8-position, adjacent to a prochiral carbon atom, was achieved by photolysis of (-)-menthyl benzenesulfenate in the presence of hexabutylditin and (1R, 3R, 4S, 8S)-9-phenylthiomenthot (4) was obtained with 91 % optical purity. High stereoselectivity of the reaction was calculated (ab initio MP2/6-3 1G**) to be the consequence of the difference in the transition state eneregies (DeltaDeltaG(#) = 5.08 kJ/mol) favouring 4 relative to (1R,3R,4S,8R)-9-phenylthiomenthoI (5). The absolute configuration of a the new chiral carbon atom was confirmed by its correlation with the corresponding menthane-3,9-diol of known stereochemistry., Fotolizom (–)-mentil-benzensulfenata u prisustvu heksabutil-dikalaja izvršeno je stereoselektivno uvođenje feniltio grupe na neaktiviranu metil grupu u δ-položaju koja je susedna prohiralnom ugljenikovom atomu i dobiven je (1R 3R, 4S, 8S)-9-feniltio-mentol (4) sa 91 % optičke čistoće. Visoka stereoselektivnost reakcije, potvrđena računom (ab initio MP2/6-21G**) posledica je razlike u energijama prelaznih stanja ΔΔG# = 5.08 kJ/mol) koja favorizuje nastajanje 4 u odnosu na (1R, 3R, 4S, 8R)-9-feniltio-mentol (5). Apsolutna konfiguracija novog hiralnog ugljenikovog atoma potvrđena je korelacijom s odgovarajućim mentan-3,9-diolom poznate stereohemije.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Stereoselective free radical phenylsulfenylation of a nonactivated delta-carbon atom, Stereoselektivno slobodnoradikalsko fenilsulfenilovanje neaktiviranog δ-ugljenikovog atoma",
volume = "69",
number = "10",
pages = "737-747",
doi = "10.2298/JSC0410737P"
}
Petrović, G., Saičić, R., Došen-Mićović, L.,& Čeković, Ž.. (2004). Stereoselective free radical phenylsulfenylation of a nonactivated delta-carbon atom. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 69(10), 737-747.
https://doi.org/10.2298/JSC0410737P
Petrović G, Saičić R, Došen-Mićović L, Čeković Ž. Stereoselective free radical phenylsulfenylation of a nonactivated delta-carbon atom. in Journal of the Serbian Chemical Society. 2004;69(10):737-747.
doi:10.2298/JSC0410737P .
Petrović, G., Saičić, Radomir, Došen-Mićović, Ljiljana, Čeković, Živorad, "Stereoselective free radical phenylsulfenylation of a nonactivated delta-carbon atom" in Journal of the Serbian Chemical Society, 69, no. 10 (2004):737-747,
https://doi.org/10.2298/JSC0410737P . .
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Regioselective free radical phenylsulfenation of a non-activated delta-carbon atom by the photolysis of alkyl benzenesulfenate

Petrović, G.; Saičić, Radomir; Čeković, Živorad

(Pergamon-Elsevier Science Ltd, Oxford, 2003)

TY  - JOUR
AU  - Petrović, G.
AU  - Saičić, Radomir
AU  - Čeković, Živorad
PY  - 2003
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/532
AB  - A regioselective free radical introduction of a phenylthio group onto a non-activated delta-carbon atom was achieved by photolysis of alkyl benzenesulfenates in the presence of hexabutylditin, and delta-phenylthio alcohols were obtained in 35-91% yields. delta-Phenylsulfenylation of a non-activated carbon atom induced only by irradiation of alkyl benzenesulfenates (without initiation by hexabutylditin) also occurs, however, slower reaction rates were observed and lower yields of delta-phenylthio alcohols were obtained. (C) 2002 Published by Elsevier Science Ltd.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - Regioselective free radical phenylsulfenation of a non-activated delta-carbon atom by the photolysis of alkyl benzenesulfenate
VL  - 59
IS  - 2
SP  - 187
EP  - 196
DO  - 10.1016/S0040-4020(02)01477-1
ER  - 
@article{
author = "Petrović, G. and Saičić, Radomir and Čeković, Živorad",
year = "2003",
abstract = "A regioselective free radical introduction of a phenylthio group onto a non-activated delta-carbon atom was achieved by photolysis of alkyl benzenesulfenates in the presence of hexabutylditin, and delta-phenylthio alcohols were obtained in 35-91% yields. delta-Phenylsulfenylation of a non-activated carbon atom induced only by irradiation of alkyl benzenesulfenates (without initiation by hexabutylditin) also occurs, however, slower reaction rates were observed and lower yields of delta-phenylthio alcohols were obtained. (C) 2002 Published by Elsevier Science Ltd.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Regioselective free radical phenylsulfenation of a non-activated delta-carbon atom by the photolysis of alkyl benzenesulfenate",
volume = "59",
number = "2",
pages = "187-196",
doi = "10.1016/S0040-4020(02)01477-1"
}
Petrović, G., Saičić, R.,& Čeković, Ž.. (2003). Regioselective free radical phenylsulfenation of a non-activated delta-carbon atom by the photolysis of alkyl benzenesulfenate. in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 59(2), 187-196.
https://doi.org/10.1016/S0040-4020(02)01477-1
Petrović G, Saičić R, Čeković Ž. Regioselective free radical phenylsulfenation of a non-activated delta-carbon atom by the photolysis of alkyl benzenesulfenate. in Tetrahedron. 2003;59(2):187-196.
doi:10.1016/S0040-4020(02)01477-1 .
Petrović, G., Saičić, Radomir, Čeković, Živorad, "Regioselective free radical phenylsulfenation of a non-activated delta-carbon atom by the photolysis of alkyl benzenesulfenate" in Tetrahedron, 59, no. 2 (2003):187-196,
https://doi.org/10.1016/S0040-4020(02)01477-1 . .
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Synthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate

Petrović, GB; Saičić, Radomir; Čeković, Živorad

(Wiley-V C H Verlag Gmbh, Weinheim, 2003)

TY  - JOUR
AU  - Petrović, GB
AU  - Saičić, Radomir
AU  - Čeković, Živorad
PY  - 2003
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/153
AB  - The synthesis of scopin acetate (6b) and 6,7-didehydrohyoscyamine (17) was achieved by using tropine (5) as the starting compound. Formal (phenylthio)-radical transfer to the nonactivated 6-position of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate (9) by irradiation in the presence of hexabutyldistannane is a key step of this synthetic approach, involving ethyl 6,7-didehydro-N-demethyltropine-N-carboxylate (15) as a synthetic intermediate (Schemes 3 and 5). The reaction of 9 with tributylstannane in the presence of ethyl acrylate, as a radicophilic olefin. involves Michael-type alkylation at C(6) of the tropine skeleton affording ethyl N-demethyl-N-(ethoxycarbonyl)tropine-6-propanoate (18) (Scheme 6).
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Helvetica Chimica Acta
T1  - Synthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate
VL  - 86
IS  - 9
SP  - 3179
EP  - 3186
DO  - 10.1002/hlca.200390258
ER  - 
@article{
author = "Petrović, GB and Saičić, Radomir and Čeković, Živorad",
year = "2003",
abstract = "The synthesis of scopin acetate (6b) and 6,7-didehydrohyoscyamine (17) was achieved by using tropine (5) as the starting compound. Formal (phenylthio)-radical transfer to the nonactivated 6-position of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate (9) by irradiation in the presence of hexabutyldistannane is a key step of this synthetic approach, involving ethyl 6,7-didehydro-N-demethyltropine-N-carboxylate (15) as a synthetic intermediate (Schemes 3 and 5). The reaction of 9 with tributylstannane in the presence of ethyl acrylate, as a radicophilic olefin. involves Michael-type alkylation at C(6) of the tropine skeleton affording ethyl N-demethyl-N-(ethoxycarbonyl)tropine-6-propanoate (18) (Scheme 6).",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Helvetica Chimica Acta",
title = "Synthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate",
volume = "86",
number = "9",
pages = "3179-3186",
doi = "10.1002/hlca.200390258"
}
Petrović, G., Saičić, R.,& Čeković, Ž.. (2003). Synthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate. in Helvetica Chimica Acta
Wiley-V C H Verlag Gmbh, Weinheim., 86(9), 3179-3186.
https://doi.org/10.1002/hlca.200390258
Petrović G, Saičić R, Čeković Ž. Synthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate. in Helvetica Chimica Acta. 2003;86(9):3179-3186.
doi:10.1002/hlca.200390258 .
Petrović, GB, Saičić, Radomir, Čeković, Živorad, "Synthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate" in Helvetica Chimica Acta, 86, no. 9 (2003):3179-3186,
https://doi.org/10.1002/hlca.200390258 . .
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Free radical domino reactions in the synthesis of small ring compounds: multiple annulation of cyclopropane-containing polycycles

Ferjančić, Zorana; Čeković, Živorad; Saičić, Radomir

(Editions Scientifiques Medicales Elsevier, Paris Cedex 15, 2001)

TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Čeković, Živorad
AU  - Saičić, Radomir
PY  - 2001
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/470
AB  - Free radical approach to fused vinylcyclopropane derivatives is described. Homolytic decomposition of Barton esters 4a-f in the presence of activated alkynes affords bicyclo[3.1.0]hex-2-ene derivatives 5a-g in moderate yields (18-52 %). The propagation sequence comprises: intermolecular addition/5-exo-cyclization/3-exo-cyclization/beta -elimination, and allows for a one-pot synthesis of bicyclic cyclopropane derivatives starting from two acyclic, unsaturated compounds. (C) 2001 Academie des sciences / Editions scientifiques et medicales Elsevier SAS.
PB  - Editions Scientifiques Medicales Elsevier, Paris Cedex 15
T2  - Comptes Rendus de L'academie des Sciences: Series IIc: Chemistry
T1  - Free radical domino reactions in the synthesis of small ring compounds: multiple annulation of cyclopropane-containing polycycles
VL  - 4
IS  - 7
SP  - 599
EP  - 610
DO  - 10.1016/S1387-1609(01)01276-2
ER  - 
@article{
author = "Ferjančić, Zorana and Čeković, Živorad and Saičić, Radomir",
year = "2001",
abstract = "Free radical approach to fused vinylcyclopropane derivatives is described. Homolytic decomposition of Barton esters 4a-f in the presence of activated alkynes affords bicyclo[3.1.0]hex-2-ene derivatives 5a-g in moderate yields (18-52 %). The propagation sequence comprises: intermolecular addition/5-exo-cyclization/3-exo-cyclization/beta -elimination, and allows for a one-pot synthesis of bicyclic cyclopropane derivatives starting from two acyclic, unsaturated compounds. (C) 2001 Academie des sciences / Editions scientifiques et medicales Elsevier SAS.",
publisher = "Editions Scientifiques Medicales Elsevier, Paris Cedex 15",
journal = "Comptes Rendus de L'academie des Sciences: Series IIc: Chemistry",
title = "Free radical domino reactions in the synthesis of small ring compounds: multiple annulation of cyclopropane-containing polycycles",
volume = "4",
number = "7",
pages = "599-610",
doi = "10.1016/S1387-1609(01)01276-2"
}
Ferjančić, Z., Čeković, Ž.,& Saičić, R.. (2001). Free radical domino reactions in the synthesis of small ring compounds: multiple annulation of cyclopropane-containing polycycles. in Comptes Rendus de L'academie des Sciences: Series IIc: Chemistry
Editions Scientifiques Medicales Elsevier, Paris Cedex 15., 4(7), 599-610.
https://doi.org/10.1016/S1387-1609(01)01276-2
Ferjančić Z, Čeković Ž, Saičić R. Free radical domino reactions in the synthesis of small ring compounds: multiple annulation of cyclopropane-containing polycycles. in Comptes Rendus de L'academie des Sciences: Series IIc: Chemistry. 2001;4(7):599-610.
doi:10.1016/S1387-1609(01)01276-2 .
Ferjančić, Zorana, Čeković, Živorad, Saičić, Radomir, "Free radical domino reactions in the synthesis of small ring compounds: multiple annulation of cyclopropane-containing polycycles" in Comptes Rendus de L'academie des Sciences: Series IIc: Chemistry, 4, no. 7 (2001):599-610,
https://doi.org/10.1016/S1387-1609(01)01276-2 . .
2
1
3
1

Intermolecular free radical additions to strained cycloalkenes. Cyclopropene and cyclobutene as radical accepters

Ferjančić, Zorana; Čeković, Živorad; Saičić, Radomir

(Pergamon-Elsevier Science Ltd, Oxford, 2000)

TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Čeković, Živorad
AU  - Saičić, Radomir
PY  - 2000
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/433
AB  - Intermolecular additions of electrophilic radicals to cyclopropene and cyclobutene derivatives afford the addition products in 37-50% yield. The strain relief in the intermediary radical accelerates the addition, as shown by competitive addition experiments. (C) 2000 Elsevier Science Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron Letters
T1  - Intermolecular free radical additions to strained cycloalkenes. Cyclopropene and cyclobutene as radical accepters
VL  - 41
IS  - 16
SP  - 2979
EP  - 2982
DO  - 10.1016/S0040-4039(00)00286-0
ER  - 
@article{
author = "Ferjančić, Zorana and Čeković, Živorad and Saičić, Radomir",
year = "2000",
abstract = "Intermolecular additions of electrophilic radicals to cyclopropene and cyclobutene derivatives afford the addition products in 37-50% yield. The strain relief in the intermediary radical accelerates the addition, as shown by competitive addition experiments. (C) 2000 Elsevier Science Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron Letters",
title = "Intermolecular free radical additions to strained cycloalkenes. Cyclopropene and cyclobutene as radical accepters",
volume = "41",
number = "16",
pages = "2979-2982",
doi = "10.1016/S0040-4039(00)00286-0"
}
Ferjančić, Z., Čeković, Ž.,& Saičić, R.. (2000). Intermolecular free radical additions to strained cycloalkenes. Cyclopropene and cyclobutene as radical accepters. in Tetrahedron Letters
Pergamon-Elsevier Science Ltd, Oxford., 41(16), 2979-2982.
https://doi.org/10.1016/S0040-4039(00)00286-0
Ferjančić Z, Čeković Ž, Saičić R. Intermolecular free radical additions to strained cycloalkenes. Cyclopropene and cyclobutene as radical accepters. in Tetrahedron Letters. 2000;41(16):2979-2982.
doi:10.1016/S0040-4039(00)00286-0 .
Ferjančić, Zorana, Čeković, Živorad, Saičić, Radomir, "Intermolecular free radical additions to strained cycloalkenes. Cyclopropene and cyclobutene as radical accepters" in Tetrahedron Letters, 41, no. 16 (2000):2979-2982,
https://doi.org/10.1016/S0040-4039(00)00286-0 . .
33
27
32
31

Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3 alpha-benzenesulfenate

Petrović, G.; Saičić, Radomir; Čeković, Živorad

(Georg Thieme Verlag, Stuttgart, 1999)

TY  - JOUR
AU  - Petrović, G.
AU  - Saičić, Radomir
AU  - Čeković, Živorad
PY  - 1999
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/415
AB  - The synthesis of acetyl scopine using tropine as a starting compound was achieved. Free radical phenylthio group transfer to the 6-position, in the reaction of N-carbethoxy nortropine-3 alpha-benzenesulfenate with hexabutylditin, is a key step of this synthetic approach to scopine. The reaction of N-carbethoxy nortropine-benzenesulfenate with tributyltin hydride in the presence of a radicophilic olefin involves Michael type alkylation at the 6-position of tropine skeleton affording 6-(2-carbethoxyethyl)-N-carbethoxy nortropine in 31% yield.
PB  - Georg Thieme Verlag, Stuttgart
T2  - Synlett
T1  - Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3 alpha-benzenesulfenate
IS  - 5
SP  - 635
EP  - 637
DO  - 10.1055/s-1999-2658
ER  - 
@article{
author = "Petrović, G. and Saičić, Radomir and Čeković, Živorad",
year = "1999",
abstract = "The synthesis of acetyl scopine using tropine as a starting compound was achieved. Free radical phenylthio group transfer to the 6-position, in the reaction of N-carbethoxy nortropine-3 alpha-benzenesulfenate with hexabutylditin, is a key step of this synthetic approach to scopine. The reaction of N-carbethoxy nortropine-benzenesulfenate with tributyltin hydride in the presence of a radicophilic olefin involves Michael type alkylation at the 6-position of tropine skeleton affording 6-(2-carbethoxyethyl)-N-carbethoxy nortropine in 31% yield.",
publisher = "Georg Thieme Verlag, Stuttgart",
journal = "Synlett",
title = "Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3 alpha-benzenesulfenate",
number = "5",
pages = "635-637",
doi = "10.1055/s-1999-2658"
}
Petrović, G., Saičić, R.,& Čeković, Ž.. (1999). Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3 alpha-benzenesulfenate. in Synlett
Georg Thieme Verlag, Stuttgart.(5), 635-637.
https://doi.org/10.1055/s-1999-2658
Petrović G, Saičić R, Čeković Ž. Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3 alpha-benzenesulfenate. in Synlett. 1999;(5):635-637.
doi:10.1055/s-1999-2658 .
Petrović, G., Saičić, Radomir, Čeković, Živorad, "Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3 alpha-benzenesulfenate" in Synlett, no. 5 (1999):635-637,
https://doi.org/10.1055/s-1999-2658 . .
3
16
20
23
16

Semisynthesis of Taxol (R): an improved procedure far the isolation of 10-deacetylbaccatin III

Saičić, Radomir; Matović, Radomir; Čeković, Živorad

(Serbian Chemical Soc, Belgrade, 1999)

TY  - JOUR
AU  - Saičić, Radomir
AU  - Matović, Radomir
AU  - Čeković, Živorad
PY  - 1999
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/419
AB  - From the needles of domestic yew, (Taxus baccata), 10-deacetylbaccatin III (10-DAB) call be isolated in quantities of up to 297 mg per kg of fresh needles. Additional quantities of 10-DAB call be obtained from the extract by NaBH4 mediated reductive hydrolysis of baccatin esters. A four-step procedure converts 10-DAB into taxol in 58% overall yield.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Semisynthesis of Taxol (R): an improved procedure far the isolation of 10-deacetylbaccatin III
VL  - 64
IS  - 9
SP  - 497
EP  - 503
UR  - https://hdl.handle.net/21.15107/rcub_cherry_419
ER  - 
@article{
author = "Saičić, Radomir and Matović, Radomir and Čeković, Živorad",
year = "1999",
abstract = "From the needles of domestic yew, (Taxus baccata), 10-deacetylbaccatin III (10-DAB) call be isolated in quantities of up to 297 mg per kg of fresh needles. Additional quantities of 10-DAB call be obtained from the extract by NaBH4 mediated reductive hydrolysis of baccatin esters. A four-step procedure converts 10-DAB into taxol in 58% overall yield.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Semisynthesis of Taxol (R): an improved procedure far the isolation of 10-deacetylbaccatin III",
volume = "64",
number = "9",
pages = "497-503",
url = "https://hdl.handle.net/21.15107/rcub_cherry_419"
}
Saičić, R., Matović, R.,& Čeković, Ž.. (1999). Semisynthesis of Taxol (R): an improved procedure far the isolation of 10-deacetylbaccatin III. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 64(9), 497-503.
https://hdl.handle.net/21.15107/rcub_cherry_419
Saičić R, Matović R, Čeković Ž. Semisynthesis of Taxol (R): an improved procedure far the isolation of 10-deacetylbaccatin III. in Journal of the Serbian Chemical Society. 1999;64(9):497-503.
https://hdl.handle.net/21.15107/rcub_cherry_419 .
Saičić, Radomir, Matović, Radomir, Čeković, Živorad, "Semisynthesis of Taxol (R): an improved procedure far the isolation of 10-deacetylbaccatin III" in Journal of the Serbian Chemical Society, 64, no. 9 (1999):497-503,
https://hdl.handle.net/21.15107/rcub_cherry_419 .
2
2

Sequential free radical reactions with xanthates: Cyclopentane ring annulation

Maslak, Veselin; Čeković, Živorad; Saičić, Radomir

(Georg Thieme Verlag, Stuttgart, 1998)

TY  - JOUR
AU  - Maslak, Veselin
AU  - Čeković, Živorad
AU  - Saičić, Radomir
PY  - 1998
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/404
AB  - In the presence of electron-rich alkenes, electro- and ambiphilic homoallylic radicals, generated by homolytic decomposition of the corresponding xanthates, undergo annulation with inverse electron-demand, and afford cyclopentane derivatives in moderate to good yields.
PB  - Georg Thieme Verlag, Stuttgart
T2  - Synlett
T1  - Sequential free radical reactions with xanthates: Cyclopentane ring annulation
IS  - 12
SP  - 1435
EP  - 1437
UR  - https://hdl.handle.net/21.15107/rcub_cherry_404
ER  - 
@article{
author = "Maslak, Veselin and Čeković, Živorad and Saičić, Radomir",
year = "1998",
abstract = "In the presence of electron-rich alkenes, electro- and ambiphilic homoallylic radicals, generated by homolytic decomposition of the corresponding xanthates, undergo annulation with inverse electron-demand, and afford cyclopentane derivatives in moderate to good yields.",
publisher = "Georg Thieme Verlag, Stuttgart",
journal = "Synlett",
title = "Sequential free radical reactions with xanthates: Cyclopentane ring annulation",
number = "12",
pages = "1435-1437",
url = "https://hdl.handle.net/21.15107/rcub_cherry_404"
}
Maslak, V., Čeković, Ž.,& Saičić, R.. (1998). Sequential free radical reactions with xanthates: Cyclopentane ring annulation. in Synlett
Georg Thieme Verlag, Stuttgart.(12), 1435-1437.
https://hdl.handle.net/21.15107/rcub_cherry_404
Maslak V, Čeković Ž, Saičić R. Sequential free radical reactions with xanthates: Cyclopentane ring annulation. in Synlett. 1998;(12):1435-1437.
https://hdl.handle.net/21.15107/rcub_cherry_404 .
Maslak, Veselin, Čeković, Živorad, Saičić, Radomir, "Sequential free radical reactions with xanthates: Cyclopentane ring annulation" in Synlett, no. 12 (1998):1435-1437,
https://hdl.handle.net/21.15107/rcub_cherry_404 .
14
20

Free radical mediated construction of small ring compounds: The double annulation of bicyclo[3.1.0]hex-2-enes

Ferjančić, Zorana; Saičić, Radomir; Čeković, Živorad

(Pergamon-Elsevier Science Ltd, Oxford, 1997)

TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
AU  - Čeković, Živorad
PY  - 1997
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2591
AB  - A free radical approach to fused cyclopropane derivatives is described. Homolytic decomposition of thiohydroxamic esters 4a-e in the presence of dimethyl acetylendicarboxylate affords bicyclo[3.1.0]hex-2-enes 6a-e in moderate yields. (C) 1997 Elsevier Science Ltd.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron Letters
T1  - Free radical mediated construction of small ring compounds: The double annulation of bicyclo[3.1.0]hex-2-enes
VL  - 38
IS  - 23
SP  - 4165
EP  - 4168
DO  - 10.1016/S0040-4039(97)00811-3
ER  - 
@article{
author = "Ferjančić, Zorana and Saičić, Radomir and Čeković, Živorad",
year = "1997",
abstract = "A free radical approach to fused cyclopropane derivatives is described. Homolytic decomposition of thiohydroxamic esters 4a-e in the presence of dimethyl acetylendicarboxylate affords bicyclo[3.1.0]hex-2-enes 6a-e in moderate yields. (C) 1997 Elsevier Science Ltd.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron Letters",
title = "Free radical mediated construction of small ring compounds: The double annulation of bicyclo[3.1.0]hex-2-enes",
volume = "38",
number = "23",
pages = "4165-4168",
doi = "10.1016/S0040-4039(97)00811-3"
}
Ferjančić, Z., Saičić, R.,& Čeković, Ž.. (1997). Free radical mediated construction of small ring compounds: The double annulation of bicyclo[3.1.0]hex-2-enes. in Tetrahedron Letters
Pergamon-Elsevier Science Ltd, Oxford., 38(23), 4165-4168.
https://doi.org/10.1016/S0040-4039(97)00811-3
Ferjančić Z, Saičić R, Čeković Ž. Free radical mediated construction of small ring compounds: The double annulation of bicyclo[3.1.0]hex-2-enes. in Tetrahedron Letters. 1997;38(23):4165-4168.
doi:10.1016/S0040-4039(97)00811-3 .
Ferjančić, Zorana, Saičić, Radomir, Čeković, Živorad, "Free radical mediated construction of small ring compounds: The double annulation of bicyclo[3.1.0]hex-2-enes" in Tetrahedron Letters, 38, no. 23 (1997):4165-4168,
https://doi.org/10.1016/S0040-4039(97)00811-3 . .
8
9
11
7

Free radical phenylthio group transfer to nonactivated delta-carbon atom in the photolysis reactions of alkyl benzenesulfenates

Petrović, G.; Saičić, Radomir; Čeković, Živorad

(Pergamon-Elsevier Science Ltd, Oxford, 1997)

TY  - JOUR
AU  - Petrović, G.
AU  - Saičić, Radomir
AU  - Čeković, Živorad
PY  - 1997
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2596
AB  - A free radical phenylthio group transfer from oxygen to the non-activated delta-carbon atom was achieved by irradiation of alkyl benzenesulfenates 1 in the presence of hexabutylditin, and delta-phenylthio alcohols 2 were obtained in 35-91% yields. However, when reactions were performed in the presence of activated olefins an alkylation of delta-carbon occured and phenylthio ethers of type 3 were obtained in modest yields. (C) 1997 Elsevier Science Ltd.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron Letters
T1  - Free radical phenylthio group transfer to nonactivated delta-carbon atom in the photolysis reactions of alkyl benzenesulfenates
VL  - 38
IS  - 40
SP  - 7107
EP  - 7110
DO  - 10.1016/S0040-4039(97)01632-8
ER  - 
@article{
author = "Petrović, G. and Saičić, Radomir and Čeković, Živorad",
year = "1997",
abstract = "A free radical phenylthio group transfer from oxygen to the non-activated delta-carbon atom was achieved by irradiation of alkyl benzenesulfenates 1 in the presence of hexabutylditin, and delta-phenylthio alcohols 2 were obtained in 35-91% yields. However, when reactions were performed in the presence of activated olefins an alkylation of delta-carbon occured and phenylthio ethers of type 3 were obtained in modest yields. (C) 1997 Elsevier Science Ltd.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron Letters",
title = "Free radical phenylthio group transfer to nonactivated delta-carbon atom in the photolysis reactions of alkyl benzenesulfenates",
volume = "38",
number = "40",
pages = "7107-7110",
doi = "10.1016/S0040-4039(97)01632-8"
}
Petrović, G., Saičić, R.,& Čeković, Ž.. (1997). Free radical phenylthio group transfer to nonactivated delta-carbon atom in the photolysis reactions of alkyl benzenesulfenates. in Tetrahedron Letters
Pergamon-Elsevier Science Ltd, Oxford., 38(40), 7107-7110.
https://doi.org/10.1016/S0040-4039(97)01632-8
Petrović G, Saičić R, Čeković Ž. Free radical phenylthio group transfer to nonactivated delta-carbon atom in the photolysis reactions of alkyl benzenesulfenates. in Tetrahedron Letters. 1997;38(40):7107-7110.
doi:10.1016/S0040-4039(97)01632-8 .
Petrović, G., Saičić, Radomir, Čeković, Živorad, "Free radical phenylthio group transfer to nonactivated delta-carbon atom in the photolysis reactions of alkyl benzenesulfenates" in Tetrahedron Letters, 38, no. 40 (1997):7107-7110,
https://doi.org/10.1016/S0040-4039(97)01632-8 . .
3
17
16
16
14

Cyclization/alkoxy radical fragmentation tandem: An efficient approach to the synthesis of bridged cyclooctane derivatives

Saičić, Radomir; Čeković, Živorad

(1997)

TY  - JOUR
AU  - Saičić, Radomir
AU  - Čeković, Živorad
PY  - 1997
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/59
AB  - In this paper an efficient synthetic approach to bridged cyclooctanone framework is described, which is based on cyclization/alkoxy radical fragmentation as a tactical combination of reactions. While the hypoiodite reaction of alcohol 11 proceeds in a normal fashion, the hypobromite reaction of the same precursor unexpectedly affords dibromo derivative 14, which, in turn, shows unusual reactivity in the presence of cesium acetate.
T2  - Journal of the Serbian Chemical Society
T1  - Cyclization/alkoxy radical fragmentation tandem: An efficient approach to the synthesis of bridged cyclooctane derivatives
VL  - 62
IS  - 9
SP  - 727
EP  - 735
UR  - https://hdl.handle.net/21.15107/rcub_cherry_59
ER  - 
@article{
author = "Saičić, Radomir and Čeković, Živorad",
year = "1997",
abstract = "In this paper an efficient synthetic approach to bridged cyclooctanone framework is described, which is based on cyclization/alkoxy radical fragmentation as a tactical combination of reactions. While the hypoiodite reaction of alcohol 11 proceeds in a normal fashion, the hypobromite reaction of the same precursor unexpectedly affords dibromo derivative 14, which, in turn, shows unusual reactivity in the presence of cesium acetate.",
journal = "Journal of the Serbian Chemical Society",
title = "Cyclization/alkoxy radical fragmentation tandem: An efficient approach to the synthesis of bridged cyclooctane derivatives",
volume = "62",
number = "9",
pages = "727-735",
url = "https://hdl.handle.net/21.15107/rcub_cherry_59"
}
Saičić, R.,& Čeković, Ž.. (1997). Cyclization/alkoxy radical fragmentation tandem: An efficient approach to the synthesis of bridged cyclooctane derivatives. in Journal of the Serbian Chemical Society, 62(9), 727-735.
https://hdl.handle.net/21.15107/rcub_cherry_59
Saičić R, Čeković Ž. Cyclization/alkoxy radical fragmentation tandem: An efficient approach to the synthesis of bridged cyclooctane derivatives. in Journal of the Serbian Chemical Society. 1997;62(9):727-735.
https://hdl.handle.net/21.15107/rcub_cherry_59 .
Saičić, Radomir, Čeković, Živorad, "Cyclization/alkoxy radical fragmentation tandem: An efficient approach to the synthesis of bridged cyclooctane derivatives" in Journal of the Serbian Chemical Society, 62, no. 9 (1997):727-735,
https://hdl.handle.net/21.15107/rcub_cherry_59 .
2

1,3-Migration of phenylthio group in the rearrangement of tertiary cyclopropylmethanols possessing an α-phenylthio group

Saičić, Radomir; Badić, J.; Čeković, Živorad

(1996)

TY  - JOUR
AU  - Saičić, Radomir
AU  - Badić, J.
AU  - Čeković, Živorad
PY  - 1996
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/61
AB  - The acid catalysed ring opening of tertiary cyclopropylmethanols 1 (R = H, vinyl, Ph), possessing a phenylthio group on the adjacent carbon atom proceeds, regioselectively and homoallylic halides 2 are obtained in 49 - 86% yields. Depending on the structure of 1 (R= Ph, SPh) and the acid used the cyclopropane ring opening follows the 1,3-migration of phenylthio group and the corresponding 1-halo-3-phenylthio-4-pentene derivatives 3 are obtained in 54-76% yields.
T2  - Journal of the Serbian Chemical Society
T1  - 1,3-Migration of phenylthio group in the rearrangement of tertiary cyclopropylmethanols possessing an α-phenylthio group
VL  - 61
IS  - 10
SP  - 841
EP  - 848
UR  - https://hdl.handle.net/21.15107/rcub_cherry_61
ER  - 
@article{
author = "Saičić, Radomir and Badić, J. and Čeković, Živorad",
year = "1996",
abstract = "The acid catalysed ring opening of tertiary cyclopropylmethanols 1 (R = H, vinyl, Ph), possessing a phenylthio group on the adjacent carbon atom proceeds, regioselectively and homoallylic halides 2 are obtained in 49 - 86% yields. Depending on the structure of 1 (R= Ph, SPh) and the acid used the cyclopropane ring opening follows the 1,3-migration of phenylthio group and the corresponding 1-halo-3-phenylthio-4-pentene derivatives 3 are obtained in 54-76% yields.",
journal = "Journal of the Serbian Chemical Society",
title = "1,3-Migration of phenylthio group in the rearrangement of tertiary cyclopropylmethanols possessing an α-phenylthio group",
volume = "61",
number = "10",
pages = "841-848",
url = "https://hdl.handle.net/21.15107/rcub_cherry_61"
}
Saičić, R., Badić, J.,& Čeković, Ž.. (1996). 1,3-Migration of phenylthio group in the rearrangement of tertiary cyclopropylmethanols possessing an α-phenylthio group. in Journal of the Serbian Chemical Society, 61(10), 841-848.
https://hdl.handle.net/21.15107/rcub_cherry_61
Saičić R, Badić J, Čeković Ž. 1,3-Migration of phenylthio group in the rearrangement of tertiary cyclopropylmethanols possessing an α-phenylthio group. in Journal of the Serbian Chemical Society. 1996;61(10):841-848.
https://hdl.handle.net/21.15107/rcub_cherry_61 .
Saičić, Radomir, Badić, J., Čeković, Živorad, "1,3-Migration of phenylthio group in the rearrangement of tertiary cyclopropylmethanols possessing an α-phenylthio group" in Journal of the Serbian Chemical Society, 61, no. 10 (1996):841-848,
https://hdl.handle.net/21.15107/rcub_cherry_61 .

Sequential free radical synthesis of a linear triquinane skeleton from an acyclic synthon

Saičić, Radomir; Čeković, Živorad

(1994)

TY  - JOUR
AU  - Saičić, Radomir
AU  - Čeković, Živorad
PY  - 1994
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/37
AB  - Regio- and stereoselective synthesis of a linear triquinane derivative was accomplished by a sequential free radical reaction, starting from an acyclic precursor. © 1994.
T2  - Tetrahedron Letters
T1  - Sequential free radical synthesis of a linear triquinane skeleton from an acyclic synthon
VL  - 35
IS  - 42
SP  - 7845
EP  - 7848
DO  - 10.1016/0040-4039(94)80133-9
ER  - 
@article{
author = "Saičić, Radomir and Čeković, Živorad",
year = "1994",
abstract = "Regio- and stereoselective synthesis of a linear triquinane derivative was accomplished by a sequential free radical reaction, starting from an acyclic precursor. © 1994.",
journal = "Tetrahedron Letters",
title = "Sequential free radical synthesis of a linear triquinane skeleton from an acyclic synthon",
volume = "35",
number = "42",
pages = "7845-7848",
doi = "10.1016/0040-4039(94)80133-9"
}
Saičić, R.,& Čeković, Ž.. (1994). Sequential free radical synthesis of a linear triquinane skeleton from an acyclic synthon. in Tetrahedron Letters, 35(42), 7845-7848.
https://doi.org/10.1016/0040-4039(94)80133-9
Saičić R, Čeković Ž. Sequential free radical synthesis of a linear triquinane skeleton from an acyclic synthon. in Tetrahedron Letters. 1994;35(42):7845-7848.
doi:10.1016/0040-4039(94)80133-9 .
Saičić, Radomir, Čeković, Živorad, "Sequential free radical synthesis of a linear triquinane skeleton from an acyclic synthon" in Tetrahedron Letters, 35, no. 42 (1994):7845-7848,
https://doi.org/10.1016/0040-4039(94)80133-9 . .
13
19
11

Sequential radical addition/cyclization/β-elimination reactions. 3-exo- and 5-exo-cycloaddition reactions of 5-phenylthio-3-pentenyl and 5-phenylthio-3-pentynyl radicals

Saičić, Radomir; Čeković, Živorad

(1992)

TY  - JOUR
AU  - Saičić, Radomir
AU  - Čeković, Živorad
PY  - 1992
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/28
AB  - Sequential radical addition/5-exo-cyclization/β-elimination reactions, accomplished by thermally or photolytically induced decompositions of O-acyl derivatives of N-hydroxypyridine-2-thione or other thiohydroxamic esters of 6-phenylthio-4-hexenoic acid 11 in the presence of an excess of radicophilic olefins, afforded the 2-vinylcyclopentane derivatives 13 in 50-90% yields, while decompositions of thiohydroxami esters or 6-phenylthio-4-hexynoic acids 24, under the same experimental conditions and in the presence of electron deficient olefins, afforded the corresponding 2-vinylidenecyclopentane (2-exo-allenic cyclopentane) derivatives 2 (61-72%). However, when decompositions of thiohydroxamic esters 39 were carried out in boiling toluene solution without radicophilic olefins, 3-exo-cyclization took place and the corresponding 2-vinylcyclopropane derivatives 40 were obtained in 43-60% yields. © 1992.
T2  - Tetrahedron
T1  - Sequential radical addition/cyclization/β-elimination reactions. 3-exo- and 5-exo-cycloaddition reactions of 5-phenylthio-3-pentenyl and 5-phenylthio-3-pentynyl radicals
VL  - 48
IS  - 41
SP  - 8975
EP  - 8992
DO  - 10.1016/S0040-4020(01)81996-7
ER  - 
@article{
author = "Saičić, Radomir and Čeković, Živorad",
year = "1992",
abstract = "Sequential radical addition/5-exo-cyclization/β-elimination reactions, accomplished by thermally or photolytically induced decompositions of O-acyl derivatives of N-hydroxypyridine-2-thione or other thiohydroxamic esters of 6-phenylthio-4-hexenoic acid 11 in the presence of an excess of radicophilic olefins, afforded the 2-vinylcyclopentane derivatives 13 in 50-90% yields, while decompositions of thiohydroxami esters or 6-phenylthio-4-hexynoic acids 24, under the same experimental conditions and in the presence of electron deficient olefins, afforded the corresponding 2-vinylidenecyclopentane (2-exo-allenic cyclopentane) derivatives 2 (61-72%). However, when decompositions of thiohydroxamic esters 39 were carried out in boiling toluene solution without radicophilic olefins, 3-exo-cyclization took place and the corresponding 2-vinylcyclopropane derivatives 40 were obtained in 43-60% yields. © 1992.",
journal = "Tetrahedron",
title = "Sequential radical addition/cyclization/β-elimination reactions. 3-exo- and 5-exo-cycloaddition reactions of 5-phenylthio-3-pentenyl and 5-phenylthio-3-pentynyl radicals",
volume = "48",
number = "41",
pages = "8975-8992",
doi = "10.1016/S0040-4020(01)81996-7"
}
Saičić, R.,& Čeković, Ž.. (1992). Sequential radical addition/cyclization/β-elimination reactions. 3-exo- and 5-exo-cycloaddition reactions of 5-phenylthio-3-pentenyl and 5-phenylthio-3-pentynyl radicals. in Tetrahedron, 48(41), 8975-8992.
https://doi.org/10.1016/S0040-4020(01)81996-7
Saičić R, Čeković Ž. Sequential radical addition/cyclization/β-elimination reactions. 3-exo- and 5-exo-cycloaddition reactions of 5-phenylthio-3-pentenyl and 5-phenylthio-3-pentynyl radicals. in Tetrahedron. 1992;48(41):8975-8992.
doi:10.1016/S0040-4020(01)81996-7 .
Saičić, Radomir, Čeković, Živorad, "Sequential radical addition/cyclization/β-elimination reactions. 3-exo- and 5-exo-cycloaddition reactions of 5-phenylthio-3-pentenyl and 5-phenylthio-3-pentynyl radicals" in Tetrahedron, 48, no. 41 (1992):8975-8992,
https://doi.org/10.1016/S0040-4020(01)81996-7 . .
18
20
15

Cyclopentane ring formation in the cycloaddition reaction of 3-alkenyl radicals to radicophilic olefins

Saičić, Radomir; Čeković, Živorad

(1990)

TY  - JOUR
AU  - Saičić, Radomir
AU  - Čeković, Živorad
PY  - 1990
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3
AB  - Regioselective additions of 3-alkenyl radicals (10 and 20) to electron deficient olefinic bonds (7 and 17), followed by intramolecular 5- exo-cyclization and repeated addition to radicophilic double bonds were investigated and combined into a sequence of reactions for the preparation of cyclopentane derivatives (9 and 19). High regioselectivity of 3-alkenyl radical (10) addition to the electron deficient olefinic bond (7) as well as of 5-exo -cyclization of intermediary 5-hexenyl type radical (11), was achieved. The fate of intermediary cyclopentylmethyl radicals (22 and 27) depends on the nature of substituents attached to radical carbon. In case of alkyl groups (22), the nucleophilic reactivity of radical intermediates was increased and an intermolecular addition reaction occurred with the formation of a new C-C bond. However, in case of aryl groups, mesomeric stabilization of the radical (27) suppress the addition reaction to the radicophilic olefinic bond, even when the latter was used in excess, in these cases only hydrogen abstraction takes place. © 1990.
T2  - Tetrahedron
T1  - Cyclopentane ring formation in the cycloaddition reaction of 3-alkenyl radicals to radicophilic olefins
VL  - 46
IS  - 10
SP  - 3627
EP  - 3640
DO  - 10.1016/S0040-4020(01)81532-5
ER  - 
@article{
author = "Saičić, Radomir and Čeković, Živorad",
year = "1990",
abstract = "Regioselective additions of 3-alkenyl radicals (10 and 20) to electron deficient olefinic bonds (7 and 17), followed by intramolecular 5- exo-cyclization and repeated addition to radicophilic double bonds were investigated and combined into a sequence of reactions for the preparation of cyclopentane derivatives (9 and 19). High regioselectivity of 3-alkenyl radical (10) addition to the electron deficient olefinic bond (7) as well as of 5-exo -cyclization of intermediary 5-hexenyl type radical (11), was achieved. The fate of intermediary cyclopentylmethyl radicals (22 and 27) depends on the nature of substituents attached to radical carbon. In case of alkyl groups (22), the nucleophilic reactivity of radical intermediates was increased and an intermolecular addition reaction occurred with the formation of a new C-C bond. However, in case of aryl groups, mesomeric stabilization of the radical (27) suppress the addition reaction to the radicophilic olefinic bond, even when the latter was used in excess, in these cases only hydrogen abstraction takes place. © 1990.",
journal = "Tetrahedron",
title = "Cyclopentane ring formation in the cycloaddition reaction of 3-alkenyl radicals to radicophilic olefins",
volume = "46",
number = "10",
pages = "3627-3640",
doi = "10.1016/S0040-4020(01)81532-5"
}
Saičić, R.,& Čeković, Ž.. (1990). Cyclopentane ring formation in the cycloaddition reaction of 3-alkenyl radicals to radicophilic olefins. in Tetrahedron, 46(10), 3627-3640.
https://doi.org/10.1016/S0040-4020(01)81532-5
Saičić R, Čeković Ž. Cyclopentane ring formation in the cycloaddition reaction of 3-alkenyl radicals to radicophilic olefins. in Tetrahedron. 1990;46(10):3627-3640.
doi:10.1016/S0040-4020(01)81532-5 .
Saičić, Radomir, Čeković, Živorad, "Cyclopentane ring formation in the cycloaddition reaction of 3-alkenyl radicals to radicophilic olefins" in Tetrahedron, 46, no. 10 (1990):3627-3640,
https://doi.org/10.1016/S0040-4020(01)81532-5 . .
10
13
9

Radical cyclization reactions. Cyclopropane ring formation by 3-exo-cyclization of 5-phenylthio-3-pentenyl radicals

Čeković, Živorad; Saičić, Radomir

(1990)

TY  - JOUR
AU  - Čeković, Živorad
AU  - Saičić, Radomir
PY  - 1990
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/19
AB  - Free radical cyclopropane ring closure was accomplished by thermal decomposition of thiohydroxamic esters of 6-phenylthio-4-hexencic acids. When the reaction was performed in the presence of acrylonitrile; an addition/cyclization/elimination process took place and the corresponding cyclopentanecarbonitriles were obtained. © 1990.
T2  - Tetrahedron Letters
T1  - Radical cyclization reactions. Cyclopropane ring formation by 3-exo-cyclization of 5-phenylthio-3-pentenyl radicals
VL  - 31
IS  - 42
SP  - 6085
EP  - 6088
DO  - 10.1016/S0040-4039(00)98035-3
ER  - 
@article{
author = "Čeković, Živorad and Saičić, Radomir",
year = "1990",
abstract = "Free radical cyclopropane ring closure was accomplished by thermal decomposition of thiohydroxamic esters of 6-phenylthio-4-hexencic acids. When the reaction was performed in the presence of acrylonitrile; an addition/cyclization/elimination process took place and the corresponding cyclopentanecarbonitriles were obtained. © 1990.",
journal = "Tetrahedron Letters",
title = "Radical cyclization reactions. Cyclopropane ring formation by 3-exo-cyclization of 5-phenylthio-3-pentenyl radicals",
volume = "31",
number = "42",
pages = "6085-6088",
doi = "10.1016/S0040-4039(00)98035-3"
}
Čeković, Ž.,& Saičić, R.. (1990). Radical cyclization reactions. Cyclopropane ring formation by 3-exo-cyclization of 5-phenylthio-3-pentenyl radicals. in Tetrahedron Letters, 31(42), 6085-6088.
https://doi.org/10.1016/S0040-4039(00)98035-3
Čeković Ž, Saičić R. Radical cyclization reactions. Cyclopropane ring formation by 3-exo-cyclization of 5-phenylthio-3-pentenyl radicals. in Tetrahedron Letters. 1990;31(42):6085-6088.
doi:10.1016/S0040-4039(00)98035-3 .
Čeković, Živorad, Saičić, Radomir, "Radical cyclization reactions. Cyclopropane ring formation by 3-exo-cyclization of 5-phenylthio-3-pentenyl radicals" in Tetrahedron Letters, 31, no. 42 (1990):6085-6088,
https://doi.org/10.1016/S0040-4039(00)98035-3 . .
34
30
34

Radical annulation methodology. 2-Vinylcyclopentane derivative formation by a 3 + 2 cycloaddition reaction

Saičić, Radomir; Čeković, Živorad

(1990)

TY  - JOUR
AU  - Saičić, Radomir
AU  - Čeković, Živorad
PY  - 1990
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/21
AB  - By thermally or photolytically induced decomposition of O-acyl derivatives of N-hydroxypyridine-2-thione or other thiohydroxamic esters, in the presence of an excess of electron deficient olefins, 2-vinylcyclopentane derivatives were obtained. This sequence of addition/cyclization/elimination reaction is mediated by a phenylthio radical. © 1990.
T2  - Tetrahedron Letters
T1  - Radical annulation methodology. 2-Vinylcyclopentane derivative formation by a 3 + 2 cycloaddition reaction
VL  - 31
IS  - 29
SP  - 4203
EP  - 4206
DO  - 10.1016/S0040-4039(00)97582-8
ER  - 
@article{
author = "Saičić, Radomir and Čeković, Živorad",
year = "1990",
abstract = "By thermally or photolytically induced decomposition of O-acyl derivatives of N-hydroxypyridine-2-thione or other thiohydroxamic esters, in the presence of an excess of electron deficient olefins, 2-vinylcyclopentane derivatives were obtained. This sequence of addition/cyclization/elimination reaction is mediated by a phenylthio radical. © 1990.",
journal = "Tetrahedron Letters",
title = "Radical annulation methodology. 2-Vinylcyclopentane derivative formation by a 3 + 2 cycloaddition reaction",
volume = "31",
number = "29",
pages = "4203-4206",
doi = "10.1016/S0040-4039(00)97582-8"
}
Saičić, R.,& Čeković, Ž.. (1990). Radical annulation methodology. 2-Vinylcyclopentane derivative formation by a 3 + 2 cycloaddition reaction. in Tetrahedron Letters, 31(29), 4203-4206.
https://doi.org/10.1016/S0040-4039(00)97582-8
Saičić R, Čeković Ž. Radical annulation methodology. 2-Vinylcyclopentane derivative formation by a 3 + 2 cycloaddition reaction. in Tetrahedron Letters. 1990;31(29):4203-4206.
doi:10.1016/S0040-4039(00)97582-8 .
Saičić, Radomir, Čeković, Živorad, "Radical annulation methodology. 2-Vinylcyclopentane derivative formation by a 3 + 2 cycloaddition reaction" in Tetrahedron Letters, 31, no. 29 (1990):4203-4206,
https://doi.org/10.1016/S0040-4039(00)97582-8 . .
8
6
8

Free radical annulation of cyclopentane ring

Čeković, Živorad; Saičić, Radomir

(1986)

TY  - JOUR
AU  - Čeković, Živorad
AU  - Saičić, Radomir
PY  - 1986
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/180
AB  - Homoallyl radical, e.g. 2, reacts with an electron-deficient olefinic bond 1 with a new CC bond forming and arising of a 5-hexenyl radical 3 which further undergoes to 5-exo-trigonal cyclization with a cyclopentane ring (4) annulation. © 1986.
T2  - Tetrahedron Letters
T1  - Free radical annulation of cyclopentane ring
VL  - 27
IS  - 48
SP  - 5893
EP  - 5896
DO  - 10.1016/S0040-4039(00)85357-5
ER  - 
@article{
author = "Čeković, Živorad and Saičić, Radomir",
year = "1986",
abstract = "Homoallyl radical, e.g. 2, reacts with an electron-deficient olefinic bond 1 with a new CC bond forming and arising of a 5-hexenyl radical 3 which further undergoes to 5-exo-trigonal cyclization with a cyclopentane ring (4) annulation. © 1986.",
journal = "Tetrahedron Letters",
title = "Free radical annulation of cyclopentane ring",
volume = "27",
number = "48",
pages = "5893-5896",
doi = "10.1016/S0040-4039(00)85357-5"
}
Čeković, Ž.,& Saičić, R.. (1986). Free radical annulation of cyclopentane ring. in Tetrahedron Letters, 27(48), 5893-5896.
https://doi.org/10.1016/S0040-4039(00)85357-5
Čeković Ž, Saičić R. Free radical annulation of cyclopentane ring. in Tetrahedron Letters. 1986;27(48):5893-5896.
doi:10.1016/S0040-4039(00)85357-5 .
Čeković, Živorad, Saičić, Radomir, "Free radical annulation of cyclopentane ring" in Tetrahedron Letters, 27, no. 48 (1986):5893-5896,
https://doi.org/10.1016/S0040-4039(00)85357-5 . .
28
40
27

Free radical carbocyclic ring reconstruction

Čeković, Živorad; Saičić, Radomir

(1986)

TY  - JOUR
AU  - Čeković, Živorad
AU  - Saičić, Radomir
PY  - 1986
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/98
AB  - Alkenyl radical generated by β-fragmentation of tertiary cyclohexyloxy radical with carbocyclic ring opening, possessing a suitably located olefinic double bond, undergoes to the intramolecular 5-exo-trigonal cyclization and a new carbocyclic ring was formed. © 1986.
T2  - Tetrahedron Letters
T1  - Free radical carbocyclic ring reconstruction
VL  - 27
IS  - 49
SP  - 5981
EP  - 5984
DO  - 10.1016/S0040-4039(00)85378-2
ER  - 
@article{
author = "Čeković, Živorad and Saičić, Radomir",
year = "1986",
abstract = "Alkenyl radical generated by β-fragmentation of tertiary cyclohexyloxy radical with carbocyclic ring opening, possessing a suitably located olefinic double bond, undergoes to the intramolecular 5-exo-trigonal cyclization and a new carbocyclic ring was formed. © 1986.",
journal = "Tetrahedron Letters",
title = "Free radical carbocyclic ring reconstruction",
volume = "27",
number = "49",
pages = "5981-5984",
doi = "10.1016/S0040-4039(00)85378-2"
}
Čeković, Ž.,& Saičić, R.. (1986). Free radical carbocyclic ring reconstruction. in Tetrahedron Letters, 27(49), 5981-5984.
https://doi.org/10.1016/S0040-4039(00)85378-2
Čeković Ž, Saičić R. Free radical carbocyclic ring reconstruction. in Tetrahedron Letters. 1986;27(49):5981-5984.
doi:10.1016/S0040-4039(00)85378-2 .
Čeković, Živorad, Saičić, Radomir, "Free radical carbocyclic ring reconstruction" in Tetrahedron Letters, 27, no. 49 (1986):5981-5984,
https://doi.org/10.1016/S0040-4039(00)85378-2 . .
8
8
7