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Synfacts 2010(5): 0559-0559
DOI: 10.1055/s-0029-1219700
DOI: 10.1055/s-0029-1219700
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Enantioselective Synthesis of Malhamensilipin A
D. K. Bedke, G. M. Shibuya, A. R. Pereira, W. H. Gerwick, C. D. Vanderwal*
University of California, Irvine and San Diego, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. April 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201005/lookinside/thumbnails/10.1055-s-0029-1219700-1.jpg)
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.