Synthesis of the C10-C24-bis-spiroacetal core of 13-desmethyl spirolide C based on a sila-stetter-acetalization process
Synthesis of the bis-spiroacetal core of 13-desmethyl spirolide C has been completed based on a sila-Stetter-acetalization process. The acylsilane and enone partners in the Stetter reaction were prepared in 7 and 11 steps, respectively, from (S) and (R)-a
The development of a convergent and efficient enantioselective synthesis of the bengamides via a common polyol intermediate
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.
Boeckman Jr., Robert K.,Clark, Tammy J.,Shook, Brian C.
p. 4532 - 4560
(2007/10/03)
A Practical Enantioselective Total Synthesis of the Bengamides B, E, and Z
(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.
Boeckman Jr., Robert K.,Clark, Tammy J.,Shook, Brian C.
p. 2109 - 2112
(2007/10/03)
Enantiodivergent syntheses of (+)- and (-)-nonactic acid and the total synthesis of nonactin
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Bartlett,Meadows,Ottow
p. 5304 - 5311
(2007/10/23)
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