title: An efficient and stereoselective synthesis of the monomeric counterpart of marinomycin A.
abstract: [structure: see text] The monomeric counterpart of marinomycin A, an antitumor-antibiotic marine natural product, was synthesized efficiently in 11 steps from the commercially available ethyl (R)-(-)-3-hydroxybutyrate. The strategy was highlighted by a crucial regio- and stereoselective cross-metathesis to form the C20-C21 double bond, enantioselective allyltitanations to control the configuration of the C17, C23, and C25 stereogenic centers, and a stereocontrolled construction of the tetraene moiety based on an original Horner-Wadsworth-Emmons olefination followed by a Pd-catalyzed cross-coupling.
authors.affiliation: Laboratoire de Chimie Organique associé au CNRS, ESPCI, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Dominique
authors.initials: D
authors.lastname: Amans
authors.forename: Véronique
authors.initials: V
authors.lastname: Bellosta
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry
chemical_list: D000475:Alkenes; D007454:Iodides; D007783:Lactones; D018942:Macrolides; D017971:Tin Compounds; C509125:marinomycin A; C031525:stannane