Total synthesis of ingenol

J Am Chem Soc. 2004 Dec 22;126(50):16300-1. doi: 10.1021/ja044123l.

Abstract

A total synthesis of the biologically important diterpene ingenol has been completed. Ring-closing olefin metathesis was used to construct the strained "inside-outside" tetracyclic skeleton, and a series of diastereoselective reactions were employed to complete the synthesis. Another naturally occurring ingenane, 20-deoxyingenol, has also been prepared.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allyl Compounds / chemistry
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Models, Molecular
  • Sulfones / chemistry

Substances

  • Allyl Compounds
  • Diterpenes
  • Sulfones
  • ingenol