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A Biomimetic Approach to Taxol: Stereoselective Synthesis of a 12‐Membered Ring Ene‐Epoxide
Author(s) -
Takahashi Takashi,
Okabe Tadashi,
Iwamoto Hajime,
Hirose Yoichiro,
Yamada Haruo,
Doi Takayuki,
Usui Shuji,
Fukazawa Yoshimasa
Publication year - 1997
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.199700006
Subject(s) - chemistry , stereoselectivity , cyanohydrin , stereocenter , epoxide , aldol condensation , stereochemistry , aldol reaction , ring (chemistry) , alkylation , intramolecular force , enantioselective synthesis , organic chemistry , catalysis
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.