title: Total synthesis of (+/-)-bipinnatin J.
abstract: [reaction: see text]. The total synthesis of (+/-)-bipinnatin J was achieved through a concise route that features the use of a silver ion promoted S(N)1-type gamma-alkylation of a siloxyfuran and a diastereoselective Cr(II)-mediated macrocyclization to provide bipinnatin J (1), wherein the remote furanone stereocenter at C10 induced the relative stereochemistry of the two additional stereocenters.
authors.affiliation: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
authors.forename: Qinhua
authors.initials: Q
authors.lastname: Huang
authors.forename: Viresh H
authors.initials: VH
authors.lastname: Rawal
mesh_terms: D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D005663:Furans; C513883:bipinnatin J