442913-41-9Relevant academic research and scientific papers
A Practical Enantioselective Total Synthesis of the Bengamides B, E, and Z
Boeckman Jr., Robert K.,Clark, Tammy J.,Shook, Brian C.
, p. 2109 - 2112 (2002)
(equation presented) A practical total synthesis of Bengamides B, E, and Z from a common polyol intermediate is described. Consecutive aldol condensations afford a protected polyol thioester side chain suitable for coupling to the Bengamides. A novel chiral phase transfer catalyzed enantioselective alkylation affords the more highly functionalized amino caprolactams required for Bengamides B and Z. Use of the 2-naphthylmethyl ether protecting group, compatible with the boron Lewis acids required for enantioselective aldol condensation, allows direct access to Bengamide B.
The development of a convergent and efficient enantioselective synthesis of the bengamides via a common polyol intermediate
Boeckman Jr., Robert K.,Clark, Tammy J.,Shook, Brian C.
, p. 4532 - 4560 (2007/10/03)
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.
