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Synthesis of taurospongin A
Boshen Wu1, Aurélie Mallinger, Jeremy Robertson
1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
Organic Letters
|May 21, 2010
Abstract:
Two new routes to the C(1-10) carboxylic acid core of taurospongin A are presented. In the first route, overall asymmetric hydration of a C(2)-C(3) alkene is achieved by Sharpless AD and selective deoxygenation at C(2); in the second route, the C(3) stereogenic center is set by Tietze asymmetric allylation. A short synthesis of the C(1'-25') fatty acid combines with the product from the first route to complete the total synthesis of taurospongin A.
