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The Development of a Convergent and Efficient Enantioselective Synthesis of the Bengamides via a Common Polyol Intermediate

✍ Scribed by Robert K. Boeckman, Jr.; Tammy J. Clark; Brian C. Shook

Publisher
John Wiley and Sons
Year
2002
Tongue
German
Weight
297 KB
Volume
85
Category
Article
ISSN
0018-019X

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✦ Synopsis

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.

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