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
Апстракт
In this model study an alternative synthetic approach to the C1–C7 fragment of epothilones was investigated. Starting from 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.
Кључне речи:
epothilones / epoxides / enol ethers / alkylations / Lewis acidsИзвор:
Journal of the Serbian Chemical Society, 2002, 67, 4, 221-228Издавач:
- Serbian Chemical Society
DOI: 10.2298/JSC0204221L
ISSN: 0352-5139
WoS: 000174953500001
Scopus: 2-s2.0-0036000422
Институција/група
IHTMTY - JOUR AU - Lalić, Gojko AU - Galonić, Danica AU - Matović, Radomir AU - Saičić, Radomir N. PY - 2002 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/51 AB - In this model study an alternative synthetic approach to the C1–C7 fragment of epothilones was investigated. Starting from 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 Society 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 - 228 DO - 10.2298/JSC0204221L ER -
@article{ author = "Lalić, Gojko and Galonić, Danica and Matović, Radomir and Saičić, Radomir N.", year = "2002", abstract = "In this model study an alternative synthetic approach to the C1–C7 fragment of epothilones was investigated. Starting from 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 Society", 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 = "221-228", doi = "10.2298/JSC0204221L" }
Lalić, G., Galonić, D., Matović, R.,& Saičić, R. N.. (2002). A model study of epothilone synthesis: An alternative synthetic approach to the C1-C7 fragment. in Journal of the Serbian Chemical Society Serbian Chemical Society., 67(4), 221-228. https://doi.org/10.2298/JSC0204221L
Lalić G, Galonić D, Matović R, Saičić RN. A model study of epothilone synthesis: An alternative synthetic approach to the C1-C7 fragment. in Journal of the Serbian Chemical Society. 2002;67(4):221-228. doi:10.2298/JSC0204221L .
Lalić, Gojko, Galonić, Danica, Matović, Radomir, Saičić, Radomir N., "A model study of epothilone synthesis: An alternative synthetic approach to the C1-C7 fragment" in Journal of the Serbian Chemical Society, 67, no. 4 (2002):221-228, https://doi.org/10.2298/JSC0204221L . .