Deconstruction-reconstruction strategy for accessing valuable polyketides. Preparation of the C15-C24 stereopentad of discodermolide |
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Authors: | Parker Kathlyn A Wang Peng |
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Affiliation: | Department of Chemistry, State University of New York at Stony Brook, Stony Brook, NY 11794, USA. kparker@notes.cc.sunysb.edu |
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Abstract: | An advanced, known intermediate for discodermolide synthesis was prepared by an efficient sequence from the readily available fermentation product oleandomycin. The scheme makes use of a new method for the direct cleavage of aminoglycosides, a critical double-bond isomerization, and a selective protection of two of three hydroxyl groups in a modified oleandolide. This synthesis illustrates a new strategy, "deconstruction-reconstruction", for accessing stereochemically complex polyketide building blocks. |
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