title: Enantioselective Total Synthesis of (+)-Iso-A82775C, a Proposed Biosynthetic Precursor of Chloropupukeananin.
abstract: (+)-Iso-A82775C is a proposed biosynthetic precursor of the chloropupukeananin family and an important intermediate for related natural products. The first enantioselective total synthesis of (+)-iso-A82775C (18 steps, 2.2% overall yield) toward the eventual biomimetic total synthesis of chloropupukeananin is described. The key steps are (1) the enantioselective Diels-Alder reaction of 4-bromo-3-hydroxy-2-pyrone with methyl 2-chloroacrylate using cinchonine as an organocatalyst and (2) the anti-selective Cu-mediated SN2' reaction to afford the axially chiral vinylallene moiety.
authors.affiliation: Department of Chemistry, Faculty of Science, Hokkaido University , Sapporo 060-0810, Japan.|Faculty of Pharmaceutical Sciences, Tokyo University of Science , Noda-shi, Chiba 278-8525, Japan.
authors.forename: Takahiro
authors.identifier: 0000-0002-3842-1025
authors.initials: T
authors.lastname: Suzuki
authors.affiliation: Graduate School of Chemical Sciences and Engineering, Hokkaido University , Sapporo 060-0810, Japan.
authors.forename: Soichiro
authors.initials: S
authors.lastname: Watanabe
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokyo University of Science , Noda-shi, Chiba 278-8525, Japan.
authors.forename: Susumu
authors.initials: S
authors.lastname: Kobayashi
authors.affiliation: Department of Chemistry, Faculty of Science, Hokkaido University , Sapporo 060-0810, Japan.
authors.forename: Keiji
authors.identifier: 0000-0002-0580-0125
authors.initials: K
authors.lastname: Tanino