title: Enantioselective Total Synthesis of (+)-Psiguadial B.
abstract: The first enantioselective total synthesis of the cytotoxic natural product (+)-psiguadial B is reported. Key features of the synthesis include (1) the enantioselective preparation of a key cyclobutane intermediate by a tandem Wolff rearrangement/asymmetric ketene addition, (2) a directed C(sp(3))-H alkenylation reaction to strategically forge the C1-C2 bond, and (3) a ring-closing metathesis to build the bridging bicyclo[4.3.1]decane terpene framework.
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Lauren M
authors.initials: LM
authors.lastname: Chapman
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Jordan C
authors.initials: JC
authors.lastname: Beck
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Linglin
authors.initials: L
authors.lastname: Wu
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Sarah E
authors.initials: SE
authors.lastname: Reisman
mesh_terms: D000473:Alkanes / Q000737:chemistry; D001688:Biological Products; D002384:Catalysis; D002626:Chemistry, Pharmaceutical; D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry; D015195:Drug Design; D008516:Medicine, Chinese Traditional; D015394:Molecular Structure; D031647:Psidium; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000473:Alkanes; D001688:Biological Products; D003503:Cyclobutanes; D013729:Terpenes; C555187:psiguadial B; C012867:decane