A biomimetic approach to taxol: Stereoselective synthesis of a 12-membered ring ene-epoxide

Article abstract of DOI:10.1002/ijch.199700006

The stereoselective synthesis of a taxol intermediate via a biomimetic route is described. Aldol condensation of γ-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.