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Synfacts 2010(5): 0559-0559  
DOI: 10.1055/s-0029-1219700
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Synthesis of Malhamensilipin A

Contributor(s): Mark Lautens, David A. Candito
D. K. Bedke, G. M. Shibuya, A. R. Pereira, W. H. Gerwick, C. D. Vanderwal*
University of California, Irvine and San Diego, USA
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

The chlorosulfolipids are an interesting class of natural products which have been isolated from organisms in the Adriatic Sea and have been implicated in food poisoning. The authors report the first enantioselective synthesis of a member of this class of natural products, malhamensilipin A. The key features of this synthesis are two stereoselective dichlorinations, a stereospecific epoxide ring opening and a final highly selective dehydrohalogenation to install the (E)-chloro­vinyl sulfate functionality.