A study towards the synthesis of (-)-atrop-abyssomicin C core
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An attempt to synthesize the cyclohexane core of antibiotic abyssomicin C is described. The initial, protecting group-free approach (relying on internal protection) failed and had to be modified, in order to allow for efficient deprotection of the acid-sensitive cyclization precursor in the penultimate synthetic step. Thus, a pyranoside structural unit was used as a latent lactone/ester functionality, which was deprotected via thioacetalization/hydrolysis/oxidation sequence, to give the δ-valerolactone-type cyclization precursor. Unfortunately, the key cyclization reaction was not feasible, even after structural modification of the cyclization precursor. Reluctance towards cyclization turned out to be a general property of (at least some) Δ7-unsaturated esters, which required the development of a new strategy for this type of transformation.
Keywords:
organic synthesis / cyclization / protecting groups / pyranoside. / natural productsSource:
Journal of the Serbian Chemical Society, 2021, 86, 12, 1305-1315Publisher:
- Belgrade : Serbian Chemical Society
DOI: 10.2298/JSC211001099S
ISSN: 0352-5139
WoS: 000744174800014
Scopus: 2-s2.0-85124622589
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http://www.doiserbia.nb.rs/Article.aspx?id=0352-51392100099Shttp://cherry.chem.bg.ac.rs/handle/123456789/5044
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Saičić, Radomir AU - Trmčić, Milena PY - 2021 UR - http://www.doiserbia.nb.rs/Article.aspx?id=0352-51392100099S UR - http://cherry.chem.bg.ac.rs/handle/123456789/5044 AB - An attempt to synthesize the cyclohexane core of antibiotic abyssomicin C is described. The initial, protecting group-free approach (relying on internal protection) failed and had to be modified, in order to allow for efficient deprotection of the acid-sensitive cyclization precursor in the penultimate synthetic step. Thus, a pyranoside structural unit was used as a latent lactone/ester functionality, which was deprotected via thioacetalization/hydrolysis/oxidation sequence, to give the δ-valerolactone-type cyclization precursor. Unfortunately, the key cyclization reaction was not feasible, even after structural modification of the cyclization precursor. Reluctance towards cyclization turned out to be a general property of (at least some) Δ7-unsaturated esters, which required the development of a new strategy for this type of transformation. PB - Belgrade : Serbian Chemical Society T2 - Journal of the Serbian Chemical Society T2 - Journal of the Serbian Chemical Society T1 - A study towards the synthesis of (-)-atrop-abyssomicin C core VL - 86 IS - 12 SP - 1305 EP - 1315 DO - 10.2298/JSC211001099S ER -
@article{ author = "Saičić, Radomir and Trmčić, Milena", year = "2021", abstract = "An attempt to synthesize the cyclohexane core of antibiotic abyssomicin C is described. The initial, protecting group-free approach (relying on internal protection) failed and had to be modified, in order to allow for efficient deprotection of the acid-sensitive cyclization precursor in the penultimate synthetic step. Thus, a pyranoside structural unit was used as a latent lactone/ester functionality, which was deprotected via thioacetalization/hydrolysis/oxidation sequence, to give the δ-valerolactone-type cyclization precursor. Unfortunately, the key cyclization reaction was not feasible, even after structural modification of the cyclization precursor. Reluctance towards cyclization turned out to be a general property of (at least some) Δ7-unsaturated esters, which required the development of a new strategy for this type of transformation.", publisher = "Belgrade : Serbian Chemical Society", journal = "Journal of the Serbian Chemical Society, Journal of the Serbian Chemical Society", title = "A study towards the synthesis of (-)-atrop-abyssomicin C core", volume = "86", number = "12", pages = "1305-1315", doi = "10.2298/JSC211001099S" }
Saičić, R.,& Trmčić, M.. (2021). A study towards the synthesis of (-)-atrop-abyssomicin C core. in Journal of the Serbian Chemical Society Belgrade : Serbian Chemical Society., 86(12), 1305-1315. https://doi.org/10.2298/JSC211001099S
Saičić R, Trmčić M. A study towards the synthesis of (-)-atrop-abyssomicin C core. in Journal of the Serbian Chemical Society. 2021;86(12):1305-1315. doi:10.2298/JSC211001099S .
Saičić, Radomir, Trmčić, Milena, "A study towards the synthesis of (-)-atrop-abyssomicin C core" in Journal of the Serbian Chemical Society, 86, no. 12 (2021):1305-1315, https://doi.org/10.2298/JSC211001099S . .