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Published on: October 4, 2019
Total synthesis of the marine metabolite (-)-clavosolide D
Peter T Seden1, Jonathan P H Charmant, Christine L Willis
1School of Chemistry, University of Bristol, Cantock's Close, Bristol, U.K.
Abstract:
The first total synthesis of the marine natural product (-)-clavosolide D is described confirming the structure of the unsymmetrical 16-membered diolide glycosylated by permethylated d-xylose moieties. Following efficient assembly of the two tetrahydropyrans using stereoselective Prins cyclizations, the side chains were introduced via an allylation/isomerization/anti cyclopropanation sequence; the final macrolactonization step was achieved under Yamaguchi conditions.
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