THE TOTAL SYNTHESIS OF SWINHOLIDE-A .3. A STEREOCONTROLLED SYNTHESIS OF (-)-PRE-SWINHOLIDE-A

Authors
PATERSON I WARD RA SMITH JD CUMMING JG YEUNG KS
Citation
I. Paterson et al., THE TOTAL SYNTHESIS OF SWINHOLIDE-A .3. A STEREOCONTROLLED SYNTHESIS OF (-)-PRE-SWINHOLIDE-A, Tetrahedron, 51(34), 1995, pp. 9437-9466
Citations number
53
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
34
Year of publication
1995
Pages
9437 - 9466
Database
ISI
SICI code
0040-4020(1995)51:34<9437:TTSOS.>2.0.ZU;2-3
Abstract
Two coupling strategies for (-)-pre-swinholide A were devised based on the analysis in Scheme 1. In the first route, a boron-mediated aldol reaction between the ethyl ketone 19 and the aldehyde 3 was used to co nstruct the C-15-C-16 bond with moderate diastereoselectivity. In the second route, a Mukaiyama aldol reaction between the methyl ketone 54 and the aldehyde 4 introduced the C-18-C-19 bond with complete stereoc ontrol.