title: Total synthesis of ingenol.
abstract: Total synthesis of ingenol, a diterpene isolated from the genus Euphorbia, was accomplished on the basis of the novel key reactions. The highly strained ingenane skeleton was constructed through an intramolecular cyclization reaction of an acetylene dicobalt complex followed by a rearrangement reaction of an epoxy alcohol. The C(3),C(4),C(5)-triol moiety was introduced by a stereoselective double dihydroxylation reaction of a diene having C(2)-C(3) and C(4)-C(5) double bonds.
authors.affiliation: Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan. ktanino@sci.hokudai.ac.jp
authors.forename: Keiji
authors.initials: K
authors.lastname: Tanino
authors.forename: Kei
authors.initials: K
authors.lastname: Onuki
authors.forename: Kohei
authors.initials: K
authors.lastname: Asano
authors.forename: Masaaki
authors.initials: M
authors.lastname: Miyashita
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Nakamura
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Takahashi
authors.forename: Isao
authors.initials: I
authors.lastname: Kuwajima
mesh_terms: D000438:Alcohols / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000737:chemistry; D028481:Euphorbia / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D004224:Diterpenes; D004852:Epoxy Compounds; C008125:ingenol