DIASTEREOSELECTIVE ALDOL REACTIONS OF BETA-SILYLOXY ETHYL KETONES - APPLICATION TO THE TOTAL SYNTHESIS OF BAFILOMYCIN-A(1)

Authors
EVANS DA CALTER MA
Citation
Da. Evans et Ma. Calter, DIASTEREOSELECTIVE ALDOL REACTIONS OF BETA-SILYLOXY ETHYL KETONES - APPLICATION TO THE TOTAL SYNTHESIS OF BAFILOMYCIN-A(1), Tetrahedron letters, 34(43), 1993, pp. 6871-6874
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
43
Year of publication
1993
Pages
6871 - 6874
Database
ISI
SICI code
0040-4039(1993)34:43<6871:DAROBE>2.0.ZU;2-A
Abstract
Studies directed toward the C-17-C18 aldol bond construction in the ma crolide antibiotic bafilomycin Al are described. The effect of the bet a-substituent in the aldol reactions of alpha-unsubstituted enolates i s documented for various model compounds. Tle stereoselectivity of thi s process is critically dependent on the C21 and C23 oxygen protecting groups. Application of this methodology to the synthesis of bafilomyc in A1 is reported.