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Synthesis of the monomeric counterpart of marinomycin A
Dominique Amans1, Laurianne Bareille, Véronique Bellosta
1Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Abstract:
An efficient and highly convergent synthesis of the monomeric counterpart of the antitumor-antibiotic marine natural product marinomycin A was achieved by using optically active titanium complexes to control the configuration of the stereogenic centers, a highly stereo- and regioselective cross-metathesis to generate the (E)-configured C20-C21 double bond, and a Horner-Wadsworth-Emmons olefination followed by a Pd-catalyzed Stille cross-coupling to construct the tetraene moiety.
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