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Synthesis of the Monomeric Counterpart of Marinomycin A

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journal contribution
posted on 2009-10-16, 00:00 authored by Dominique Amans, Laurianne Bareille, Véronique Bellosta, Janine Cossy
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.