title: Phosphoric acid catalyzed desymmetrization of bicyclic bislactones bearing an all-carbon stereogenic center: total syntheses of (-)-rhazinilam and (-)-leucomidine B.
abstract: In the presence of a catalytic amount of an imidodiphosphoric acid, enantioselective desymmetrization of bicyclic bislactones by reaction with alcohols took place smoothly to afford enantiomerically enriched monoacids having an all-carbon stereogenic center. Concise catalytic enantioselective syntheses of both (-)-rhazinilam and (-)-leucomidine B were subsequently developed using (S)-methyl 4-ethyl-4-formylpimelate monoacid as a common starting material.
authors.affiliation: Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304. 1015 Lausanne (Switzerland) http://lspn.epfl.ch.
authors.forename: Jean-Baptiste
authors.initials: JB
authors.lastname: Gualtierotti
authors.forename: Delphine
authors.initials: D
authors.lastname: Pasche
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D001688:Biological Products; D002244:Carbon; D002384:Catalysis; D007212:Indolizines / Q000737:chemistry; D007769:Lactams / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001688:Biological Products; D007212:Indolizines; D007769:Lactams; D010756:Phosphoric Acids; C009170:rhazinilam; D002244:Carbon; C030242:phosphoric acid
keywords: alkaloids; natural products; organocatalysis; synthetic methods; total synthesis