Total synthesis of ingenol.
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.
Tanino
Keiji
K
Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan. ktanino@sci.hokudai.ac.jp
Onuki
Kei
K
Asano
Kohei
K
Miyashita
Masaaki
M
Nakamura
Tsuyoshi
T
Takahashi
Yoshinori
Y
Kuwajima
Isao
I
D000438:Alcohols / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000737:chemistry; D028481:Euphorbia / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D004224:Diterpenes; D004852:Epoxy Compounds; C008125:ingenol