Total synthesis of ingenol

Andrew Nickel; Toru Maruyama; Haifeng Tang; Prescott D Murphy; Blake Greene; Naeem Yusuff; John L Wood

doi:10.1021/ja044123l

Total synthesis of ingenol

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

Authors

Andrew Nickel¹, Toru Maruyama, Haifeng Tang, Prescott D Murphy, Blake Greene, Naeem Yusuff, John L Wood

Affiliation

¹ Sterling Chemistry Laboratory, Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.

PMID: 15600313
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