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Synfacts 2010(2): 0136-0136  
DOI: 10.1055/s-0029-1219031
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Formal Synthesis of (+)-Neopeltolide

Contributor(s): Philip Kocienski
H. Kim, Y. Park, J. Hong*
Duke University, Durham, USA
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Publication History

Publication Date:
21 January 2010 (online)

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Significance

The key step in this synthesis of the 2,6-cis-THP ring system of (+)-neopeltolide is a tandem allylic oxidation/oxa-Michael addition of an alcohol to an α,β-unsaturated aldehyde promoted by the Thorpe-Ingold effect of the dithiane ring (I → J → L).