ENANTIOSELECTIVE SYNTHESIS OF THE C1-C9 SEGMENT OF BRYOSTATIN BY KINETIC RESOLUTION OF RACEMIC ALPHA-KETO ESTERS

Authors
KALESSE M EH R
Citation
M. Kalesse et R. Eh, ENANTIOSELECTIVE SYNTHESIS OF THE C1-C9 SEGMENT OF BRYOSTATIN BY KINETIC RESOLUTION OF RACEMIC ALPHA-KETO ESTERS, Tetrahedron letters, 37(11), 1996, pp. 1767-1770
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
11
Year of publication
1996
Pages
1767 - 1770
Database
ISI
SICI code
0040-4039(1996)37:11<1767:ESOTCS>2.0.ZU;2-L
Abstract
The enantioselective synthesis of the C1-C9 segment of bryostatins is described. Racemic beta-keto ester 2 was subjected to kinetic resoluti on. Reduction with baker's yeast establishes two of the three chiral c enters. Chemical transformation of the terminal acetylene moiety gener ates aldehyde 5 which is transformed diastereoselectively to the corre sponding alcohol 6 via Sakurai reaction.