title: A catalytic, asymmetric formal synthesis of (+)-hamigeran B.
abstract: A concise asymmetric, formal synthesis of (+)-hamigeran B is reported. A Pd-catalyzed, decarboxylative allylic alkylation, employing a trifluoromethylated derivative of t-BuPHOX, is utilized as the enantioselective step to form the critical quaternary carbon center in excellent yield and enantioselectivity. The product is converted in three steps to a late-stage intermediate previously used in the synthesis of hamigeran B.
authors.affiliation: The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, California Institute of Technology, Pasadena, California 91125, USA.
authors.forename: Herschel
authors.initials: H
authors.lastname: Mukherjee
authors.forename: Nolan T
authors.initials: NT
authors.lastname: McDougal
authors.forename: Scott C
authors.initials: SC
authors.lastname: Virgil
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
mesh_terms: D000478:Alkylation; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D009285:Naphthoquinones; C483756:hamigeran B; D010165:Palladium