In this model study an alternative synthetic approach to the C1-C7 fragment of epothilones was investigated. Starting froth 4,4-dimethylcyclopentenone, a 7 step reaction sequence afforded the key intermediate 7 in 27%, overall yield. Surprisingly, the attempted deprotection of latent functionalities in 7 failed, indicating the incompatibility of the ethoxyethyl protective group with the reaction conditions employed.
U okviru model studije ispitivan je alternativni sintetički pristup C1–C7 fragmentu molekula epotilona. Polazeći od 4,4-dimetilciklopentenona, ključni intermedijer 7 dobijen je u sedam faza, u ukupnom prinosu od 27 %. Deprotekciju latentnih funkcionalnih grupa u molekulu 7 nije bilo moguće izvršiti, zbog iznenađujuće labilnosti etoksietil zaštitne grupe u baznim reakcionim uslovima.
TY - JOUR
AU - Lalic, G
AU - Galonic, D
AU - Matović, Radomir
AU - Saičić, Radomir
PY - 2002
UR - http://cherry.chem.bg.ac.rs/handle/123456789/489
AB - In this model study an alternative synthetic approach to the C1-C7 fragment of epothilones was investigated. Starting froth 4,4-dimethylcyclopentenone, a 7 step reaction sequence afforded the key intermediate 7 in 27%, overall yield. Surprisingly, the attempted deprotection of latent functionalities in 7 failed, indicating the incompatibility of the ethoxyethyl protective group with the reaction conditions employed.
AB - U okviru model studije ispitivan je alternativni sintetički pristup C1–C7 fragmentu molekula epotilona. Polazeći od 4,4-dimetilciklopentenona, ključni intermedijer 7 dobijen je u sedam faza, u ukupnom prinosu od 27 %. Deprotekciju latentnih funkcionalnih grupa u molekulu 7 nije bilo moguće izvršiti, zbog iznenađujuće labilnosti etoksietil zaštitne grupe u baznim reakcionim uslovima.
PB - Serbian Chemical Soc, Belgrade
T2 - Journal of the Serbian Chemical Society
T1 - A model study of epothilone synthesis: an alternative synthetic approach to the C1-C7 fragment
T1 - Model studija u sintezi epotilona - alternativni pristup sintezi C1-C7 fragmenta
VL - 67
IS - 4
SP - 221
EP - 227
DO - 10.2298/JSC0204221L
ER -
@article{
author = "Lalic, G and Galonic, D and Matović, Radomir and Saičić, Radomir",
year = "2002",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/489",
abstract = "In this model study an alternative synthetic approach to the C1-C7 fragment of epothilones was investigated. Starting froth 4,4-dimethylcyclopentenone, a 7 step reaction sequence afforded the key intermediate 7 in 27%, overall yield. Surprisingly, the attempted deprotection of latent functionalities in 7 failed, indicating the incompatibility of the ethoxyethyl protective group with the reaction conditions employed., U okviru model studije ispitivan je alternativni sintetički pristup C1–C7 fragmentu molekula epotilona. Polazeći od 4,4-dimetilciklopentenona, ključni intermedijer 7 dobijen je u sedam faza, u ukupnom prinosu od 27 %. Deprotekciju latentnih funkcionalnih grupa u molekulu 7 nije bilo moguće izvršiti, zbog iznenađujuće labilnosti etoksietil zaštitne grupe u baznim reakcionim uslovima.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "A model study of epothilone synthesis: an alternative synthetic approach to the C1-C7 fragment, Model studija u sintezi epotilona - alternativni pristup sintezi C1-C7 fragmenta",
volume = "67",
number = "4",
pages = "221-227",
doi = "10.2298/JSC0204221L"
}
Lalic, G., Galonic, D., Matović, R.,& Saičić, R. (2002). Model studija u sintezi epotilona - alternativni pristup sintezi C1-C7 fragmenta.
Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 67(4), 221-227.
https://doi.org/10.2298/JSC0204221L
Lalic G, Galonic D, Matović R, Saičić R. Model studija u sintezi epotilona - alternativni pristup sintezi C1-C7 fragmenta. Journal of the Serbian Chemical Society. 2002;67(4):221-227
Lalic G, Galonic D, Matović Radomir, Saičić Radomir, "Model studija u sintezi epotilona - alternativni pristup sintezi C1-C7 fragmenta" Journal of the Serbian Chemical Society, 67, no. 4 (2002):221-227,
https://doi.org/10.2298/JSC0204221L .
