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Synfacts 2014; 10(1): 0002
DOI: 10.1055/s-0033-1340355
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Short Total Synthesis of (±)-Mytilipin A

Contributor(s):
Erick M. Carreira
,
Hannes F. Zipfel
Chung W.-J, Carlson JS, Bedke DK, Vanderwal CD * University of California, Irvine and Amgen, Inc., South San Francisco, USA
A Synthesis of the Chlorosulfolipid Mytilipin A via a Longest Linear Sequence of Seven Steps.

Angew. Chem. Int. Ed. 2013;
52: 10052-10055
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Further Information

Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

chlorosulfolipids - olefin metathesis - allylation

Significance

Mytilipin A is a member of the chlorosulfolipid family of natural products. It was isolated from the mussel Mytilus galloprovincialis and is associated with seafood poisoning. In addition to their previous syntheses of other polychlorinated natural products (J. Am. Chem. Soc. 2009, 131, 7570; J. Am. Chem. Soc. 2010, 132, 2542), the authors describe a short access to mytilipin A.


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Comment

Dichloroalkohol A was oxidized with DMP and the sensitive aldehyde was directly subjected to a highly diastereoselective allylation with B to give D after basic work-up. cis‑Selective metathesis with E yielded G in 30% yield but allowed the synthesis to be finished in only another three steps. In total, (±)‑mytilipin A was prepared in seven linear steps and in more than 8% yield. The authors also describe a kinetic resolution of epoxide D, so that an enantioselective synthesis is possible with the same route.


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