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Synfacts 2009(3): 0298-0298  
DOI: 10.1055/s-0028-1087751
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

A One-Pot Protocol for the Divergent Synthesis of Dihydrofuranones

Contributor(s): Mark Lautens, David A. Candito
D. M. Hodgson*, D. Angrish, S. P. Erickson, J. Kloesges, C. H. Lee
University of Oxford, UK
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Publikationsdatum:
19. Februar 2009 (online)

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Significance

The authors report a one-pot strategy where alkene cross-metathesis is coupled to oxonium ylide formation and subsequent [2,3]-sigmatropic rearrangement. The strategy was successfully applied to the divergent synthesis of dihydrofuranones and anti-HIV agent hyperlactone C. This is an advancement from previous work where alkene cross-metathesis was coupled to carbonyl ylide formation and subsequent 1,3-dipolar cycloaddition (Adv. Synth. Catal. 2006, 348, 2509).