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. 2003 Feb 12;125(6):1498-500.
doi: 10.1021/ja029226n.

Total synthesis of ingenol

Keiji Tanino  1 , Kei Onuki, Kohei Asano, Masaaki Miyashita, Tsuyoshi Nakamura, Yoshinori Takahashi, Isao Kuwajima
Affiliations

Total synthesis of ingenol

Keiji Tanino et al. J Am Chem Soc. .

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.

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