title: One-Step Homologation for the Catalytic Asymmetric Synthesis of Deoxypropionates.
abstract: A one-step homologation protocol for the synthesis of natural products containing deoxypropionate motif is described by the combination of Zr-catalyzed asymmetric carboalumination of alkenes (ZACA)-Pd-catalyzed vinylation and ZACA-oxidation reaction. In contrast to most other synthetic strategies used to date that typically require three steps per deoxypropionate unit due to the functional-group interconversions, our one-step homologation strategy promises to provide a general and more efficient synthetic route toward deoxypropionate natural products as exemplified by significant improvements in the syntheses of intermediates and/or final products of mycolipenic acid 1 and its analogue 2, (-)-rasfonin, and syn- and anti-dicarboxylic acids 5 and 6.
authors.affiliation: Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana, 47907-2084, USA), Fax.
authors.forename: Shiqing
authors.initials: S
authors.lastname: Xu
authors.affiliation: Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana, 47907-2084, USA), Fax.
authors.forename: Haijun
authors.initials: H
authors.lastname: Li
authors.affiliation: Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana, 47907-2084, USA), Fax.
authors.forename: Masato
authors.initials: M
authors.lastname: Komiyama
authors.affiliation: Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana, 47907-2084, USA), Fax.
authors.forename: Akimichi
authors.initials: A
authors.lastname: Oda
authors.affiliation: Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana, 47907-2084, USA), Fax.
authors.forename: Ei-Ichi
authors.initials: EI
authors.lastname: Negishi
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003998:Dicarboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D011422:Propionates / Q000138:chemical synthesis / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry*
chemical_list: D001688:Biological Products; D003998:Dicarboxylic Acids; D005231:Fatty Acids, Unsaturated; D011422:Propionates; D011753:Pyrones; C416827:rasfonin; D010165:Palladium; D015040:Zirconium
keywords: ZACA reaction; asymmetric catalysis; cross-coupling; deoxypropionates; natural product synthesis