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- Title
The Development of a Convergent and Efficient Enantioselective Synthesis of the Bengamides via a Common Polyol Intermediate.
- Authors
Boeckman, Jr., Robert K.; Clark, Tammy J.; Shook, Brian C.
- Abstract
An efficient, general synthetic route to the bengamide family of antitumor agents from a common polyol thioester is described. Consecutive aldol condensations afford the protected polyol thioester side chain suitable for coupling to the bengamides. A novel chiral-phase-transfer-catalyzed enantioselective alkylation affords the properly functionalized caprolactams required for the synthesis of more-complex members of the bengamide family. Use of the methyl 2-naphthyl ether protecting group, compatible with the boron Lewis acids required for enantioselective aldol condensation, allows direct access to all the bengamides.
- Publication
Helvetica Chimica Acta, 2002, Vol 85, Issue 12, p4532
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.200290026