A BIOMIMETIC APPROACH TO TAXOL - STEREOSELECTIVE SYNTHESIS OF A 12-MEMBERED RING ENE-EPOXIDE

Authors
TAKAHASHI T OKABE T IWAMOTO H HIROSE Y YAMADA H DOI T USUI S FUKAZAWA Y
Citation
T. Takahashi et al., A BIOMIMETIC APPROACH TO TAXOL - STEREOSELECTIVE SYNTHESIS OF A 12-MEMBERED RING ENE-EPOXIDE, Israel Journal of Chemistry, 37(1), 1997, pp. 31-37
Citations number
30
Categorie Soggetti
Chemistry
Journal title
Israel Journal of Chemistry → ACNP
ISSN journal
00212148
Volume
37
Issue
1
Year of publication
1997
Pages
31 - 37
Database
ISI
SICI code
0021-2148(1997)37:1<31:ABATT->2.0.ZU;2-X
Abstract
The stereoselective synthesis of a taxol intermediate via a biomimetic route is described. Aldol condensation of gamma-butyrolactone and cit ral derivatives generated three stereogenic centers at positions C1, C 2, and C11 corresponding to taxol. Intramolecular alkylation of the cy anohydrin ether efficiently formed the 12-membered ring system in whic h stereoselective reduction, followed by directed epoxidation, afforde d the key intermediate epoxide.