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
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.
Keywords:
epothilones / epoxides / epoxides / enol ethers / enol ethers / alkylations / alkylations / Lewis acids / Lewis acidsSource:
Journal of the Serbian Chemical Society, 2002, 67, 4, 221-227Publisher:
- Serbian Chemical Soc, Belgrade
DOI: 10.2298/JSC0204221L
ISSN: 0352-5139