NOZAKI-KISHI REACTION OF CROTONATES AS A SOURCE OF COMPLEX DIENOPHILES - APPLICATION TO THE B-SECO TAXANE SERIES

Authors
QUENEAU Y KROL WJ BORNMANN WG DANISHEFSKY SJ
Citation
Y. Queneau et al., NOZAKI-KISHI REACTION OF CROTONATES AS A SOURCE OF COMPLEX DIENOPHILES - APPLICATION TO THE B-SECO TAXANE SERIES, Bulletin de la Societe chimique de France, 130(3), 1993, pp. 358-370
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
130
Issue
3
Year of publication
1993
Pages
358 - 370
Database
ISI
SICI code
0037-8968(1993)130:3<358:NROCAA>2.0.ZU;2-Y
Abstract
The Nozaki-Kishi coupling reaction between aldehyde 10 and 3-iodo-(E)- crotonate derivatives is used to produce functionalized allylic alcoho ls which served as precursors of highly substituted enones. Diels-Alde r reactions of various dienophiles derived from this chemistry, with 1 -methoxy-3-trimethylsilyloxybuta-1,3-diene are described. In this way, highly oxygenated B-seco taxane derivatives are obtained in a concise fashion.