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The Development of a Convergent and Efficient Enantioselective Synthesis of the Bengamides via a Common Polyol Intermediate
Author(s) -
Boeckman, Jr. Robert K.,
Clark Tammy J.,
Shook Brian C.
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200290026
Subject(s) - chemistry , enantioselective synthesis , polyol , aldol condensation , thioester , alkylation , aldol reaction , ether , protecting group , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , alkyl , polyurethane , enzyme
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.