ASYMMETRIC TOTAL SYNTHESIS OF CURACIN-A

Authors
ONODA T SHIRAI R KOISO Y IWASAKI S
Citation
T. Onoda et al., ASYMMETRIC TOTAL SYNTHESIS OF CURACIN-A, Tetrahedron letters, 37(25), 1996, pp. 4397-4400
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
25
Year of publication
1996
Pages
4397 - 4400
Database
ISI
SICI code
0040-4039(1996)37:25<4397:ATSOC>2.0.ZU;2-O
Abstract
Curacin A (1), a novel antimitotic agent, was synthesized in a highly stereo-controlled manner. The key steps were (1) an asymmetric allylat ion using a chiral allyltitanium reagent and a double-asymmetric Simmo ns-Smith cyclopropanation to introduce three chiral centers, (2) Witti g and Wittig-Horner reactions to construct the C(3-4) and C(7-10) alke nes, and (3) a direct conversion of the thiazolidine to the thiazoline . Copyright (C) 1996 Elsevier Science Ltd