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Letter

Synthesis of (+)-Didemniserinolipid B via Ketalization/Ring-Closing Metathesis

Christopher C. Marvin, Eric A. Voight, and Steven D. Burke*

Department of Chemistry, University of WisconsinMadison, 1101 University Avenue, Madison, Wisconsin 53706-1322

Org. Lett., 2007, 9 (26), pp 5357–5359

DOI: 10.1021/ol702454m

Publication Date (Web): November 30, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, burke@chem.wisc.edu

Abstract

A modular synthesis of didemniserinolipid B is reported. Central to this synthesis was the use of a ketalization/ring-closing metathesis (K/RCM) strategy to establish the 6,8-dioxabicyclo[3.2.1]octane core. The C10 axial alcohol was established via a selective epoxidation, followed by reductive trans-diaxial epoxide opening. The serinol and unsaturated ester side chains were introduced by a Williamson etherification and cross metathesis, respectively.

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Published In Issue December 20, 2007
Received October 8, 2007

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Letter

Synthesis of (+)-Didemniserinolipid B via Ketalization/Ring-Closing Metathesis