Synthesis of the monomeric counterpart of marinomycin A.
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.
Amans
Dominique
D
Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Bareille
Laurianne
L
Bellosta
Véronique
V
Cossy
Janine
J
D000475:Alkenes / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D019281:Dimerization; D018942:Macrolides / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry
D000475:Alkenes; D000970:Antineoplastic Agents; D018942:Macrolides; C509125:marinomycin A; D010165:Palladium