T Takahashi, T Okabe, H Iwamoto, Y Hirose, H Yamada, T Doi, S Usui, Y Fukazawa
ISRAEL JOURNAL OF CHEMISTRY 37(1) 31-37 1997年
The stereoselective synthesis of a taxol intermediate via a biomimetic route is described. Aldol condensation of gamma-butyrolactone and citral derivatives generated three stereogenic centers at positions C1, C2, and C11 corresponding to taxol. Intramolecular alkylation of the cyanohydrin ether efficiently formed the 12-membered ring system in which stereoselective reduction, followed by directed epoxidation, afforded the key intermediate epoxide.