title: Catalytic asymmetric synthesis of both syn- and anti-3,5-dihydroxy esters: application to 1,3-polyol/alpha-pyrone natural product synthesis.
abstract: [reaction: see text] We describe a catalytic asymmetric synthesis of both syn- and anti-3,5-dihydroxy esters. The method relies upon catalytic asymmetric epoxidation of alpha,beta-unsaturated imidazolides and amides, using lanthanide-BINOL complexes, and diastereoselective reduction of ketones. The method was applied to the enantioselective syntheses of 1,3-polyol/alpha-pyrone natural products 9a, 9b, and strictifolione (10). The absolute stereochemistry of 9a and 9b was also determined.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Shin-Ya
authors.initials: SY
authors.lastname: Tosaki
authors.forename: Tetsuhiro
authors.initials: T
authors.lastname: Nemoto
authors.forename: Takashi
authors.initials: T
authors.lastname: Ohshima
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: D001685:Biological Factors / Q000138:chemical synthesis; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D006880:Hydroxy Acids / Q000138:chemical synthesis*; D011753:Pyrones / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001685:Biological Factors; D004952:Esters; D006880:Hydroxy Acids; D011753:Pyrones