Studies in marine polypropionate synthesis: Total synthesis of (-)-baconipyrone C

Authors
Paterson, L Chen, DYK Acena, JL Franklin, AS
Citation
L. Paterson et al., Studies in marine polypropionate synthesis: Total synthesis of (-)-baconipyrone C, ORG LETT, 2(11), 2000, pp. 1513-1516
Citations number
32
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
11
Year of publication
2000
Pages
1513 - 1516
Database
ISI
SICI code
1523-7060(20000601)2:11<1513:SIMPST>2.0.ZU;2-4
Abstract
[GRAPHICS] An asymmetric total synthesis of the unusual siphonariid metabolite, (-)-ba conipyrone C (3), is described. Key steps included a tin(II)-mediated aldol coupling for the preparation of the carboxylic acid 17 and two different b oron mediated aldol additions leading to alcohol 8. Ester formation using m odified Yamaguchi conditions gave 24, leading on PMB deprotection to (-)-ba conipyrone C.