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Synthesis 2012; 44(16): 2595-2600
DOI: 10.1055/s-0032-1316561
DOI: 10.1055/s-0032-1316561
paper
Total Synthesis of (–)-Invictolide
Further Information
Publication History
Received: 11 April 2012
Accepted after revision: 22 May 2012
Publication Date:
06 July 2012 (online)
Abstract
A convergent approach to the total synthesis of (–)-invictolide, a component of the queen recognition pheromone of Solenopsis invicta, is described. Key steps involve the desymmetrization of a bicyclic olefin with Brown’s chiral hydroboration, C–C bond formation, 1,3-syn reduction, and oxidative lactonization of a 1,3,5-triol with TEMPO/PhI(OAc)2.
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For the synthesis of racemic invictolide:
For the synthesis of optically active invictolide: