title: Total synthesis of zincophorin and its methyl ester.
abstract: A total synthesis of the naturally occurring ionophore zincophorin has been realized. The route features an intramolecular oxymercuration of a cyclopropanemethanol and a Carroll-Claisen rearrangement for the respective elaboration of the C1-C12 and C13-C25 subunits, which have been assembled by using a highly diastereoselective titanium-mediated aldol condensation.
authors.affiliation: Laboratoire de Chimie Organique, asocié au CNRS, ESPCI, 10 rue Vauquelin 75231 Paris Cedex 05 - France.
authors.forename: Magali
authors.initials: M
authors.lastname: Defosseux
authors.forename: Nicolas
authors.initials: N
authors.lastname: Blanchard
authors.forename: Christophe
authors.initials: C
authors.lastname: Meyer
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D007202:Indicators and Reagents; D015394:Molecular Structure; D011422:Propionates; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D002264:Carboxylic Acids; D004952:Esters; D007202:Indicators and Reagents; D011422:Propionates; C488419:zincophorin methyl ester; C043279:zincophorin