title: Total Synthesis of (+)-(2S,3R)-Piscidic Acid via Catalytic Asymmetric Dihydroxylation of a Trisubstituted Olefin.
abstract: (+)-(2S,3R)-Piscidic acid was efficiently synthesized with high optical purity (90% e.e.) via Sharpless catalytic asymmetric dihydroxylation of a trisubstituted olefin in only 6 steps from commercially available 4-hydroxyphenylpyruvic acid as the starting material. The reaction proceeded with high optical purity by using the chiral ligands, dihydroquinidine 2,5-diphenyl-4,6-pyrimidinediyl diether or dihydroquinidine 1,4-anthraquinonediyl diether.
authors.affiliation: a Department of Bioscience and Chemistry, Faculty of Agriculture, Hokkaido University.
authors.forename: H
authors.initials: H
authors.lastname: Toshima
authors.affiliation: a Department of Bioscience and Chemistry, Faculty of Agriculture, Hokkaido University.
authors.forename: M
authors.initials: M
authors.lastname: Saito
authors.affiliation: a Department of Bioscience and Chemistry, Faculty of Agriculture, Hokkaido University.
authors.forename: T
authors.initials: T
authors.lastname: Yoshihara
keywords: asymmetric dihydroxylation; catalytic asymmetric synthesis; piscidic acid