A PRACTICAL, ENANTIOSELECTIVE SYNTHESIS OF SK-AND-F 104353

Citation
Jr. Flisak et al., A PRACTICAL, ENANTIOSELECTIVE SYNTHESIS OF SK-AND-F 104353, Journal of organic chemistry, 58(23), 1993, pp. 6247-6254
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
58
Issue
23
Year of publication
1993
Pages
6247 - 6254
Database
ISI
SICI code
0022-3263(1993)58:23<6247:APESOS>2.0.ZU;2-K
Abstract
A highly efficient and enantioselective (>99.5% ee) synthesis of the t itle compound has been accomplished. Key steps include (1) epoxidation of unsaturated ketone 7 in the presence of a polyamino acid to afford compound 8 in >95% ee, (2) regioselective Baeyer-Villiger rearrangeme nt of epoxy ketone 8 to afford glycidic ester 9, and (3) regioselectiv e (35:1) opening of lithium glycidate 13 at C-3 with methyl 3-mercapto propionate. The approach is economical, and all transformations procee d in high yield and are amenable to large-scale preparation.