TOTAL SYNTHESIS OF TAXOL .2. CONSTRUCTION OF A-RING AND C-RING INTERMEDIATES AND INITIAL ATTEMPTS TO CONSTRUCT THE ABC RING-SYSTEM

Authors
NICOLAOU KC LIU JJ YANG Z UENO H SORENSEN EJ CLAIBORNE CF GUY RK HWANG CK NAKADA M NANTERMET PG
Citation
Kc. Nicolaou et al., TOTAL SYNTHESIS OF TAXOL .2. CONSTRUCTION OF A-RING AND C-RING INTERMEDIATES AND INITIAL ATTEMPTS TO CONSTRUCT THE ABC RING-SYSTEM, Journal of the American Chemical Society, 117(2), 1995, pp. 634-644
Citations number
66
Categorie Soggetti
Chemistry
Journal title
Journal of the American Chemical Society → ACNP
ISSN journal
00027863
Volume
117
Issue
2
Year of publication
1995
Pages
634 - 644
Database
ISI
SICI code
0002-7863(1995)117:2<634:TSOT.C>2.0.ZU;2-H
Abstract
A method for the formation of Taxol's ABC ring system has been develop ed. General methods for the synthesis of versatile synthons for Taxol' s A ring (8) and C ring (55) are presented. A model study using a simp lified C ring synthon (17) confirmed the viability of the sequential S hapiro-McMurry strategy for formation of Taxol's B ring. Careful explo ration of the chemistry of various A-B ring conjugates allowed the dev elopment of a successful method for formation of the B ring in a more functionalized system.