Total Synthesis of Ingenol
- 17 January 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (6) , 1498-1500
- https://doi.org/10.1021/ja029226n
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.Keywords
This publication has 18 references indexed in Scilit:
- The First Total Synthesis of (±)-IngenolJournal of the American Chemical Society, 2002
- Synthesis and Biological Evaluation of Highly Functionalized Analogues of IngenolJournal of the American Chemical Society, 1998
- A New Approach for Ingenol SynthesisThe Journal of Organic Chemistry, 1997
- Recent Advances in the synthesis of Tumor-Promoting DiterpenesPublished by Elsevier ,1993
- Total synthesis of glycinoeclepin AJournal of the American Chemical Society, 1988
- Inside-outside stereoisomerism. II. Synthesis of the carbocyclic ring system of the ingenane diterpenes via the intramolecular dioxolenone photocycloadditionJournal of the American Chemical Society, 1987
- Epoxy silyl ether rearrangements: a new, stereoselective approach to the synthesis of .beta.-hydroxy carbonyl compoundsJournal of the American Chemical Society, 1986
- Antileukemic Principles Isolated from Euphorbiaceae PlantsScience, 1976
- Structure determination of the new tetracyclic diterpene ingenol-triacetate with triple product methodsTetrahedron Letters, 1970
- Bromohydrin formation in dimethyl sulfoxideJournal of the American Chemical Society, 1968