Concise synthesis of the chemopreventitive agent (+/-)-deguelin via a key 6-endo hydroarylation

Stefan J Pastine; Dalibor Sames

doi:10.1021/ol035419j

Concise synthesis of the chemopreventitive agent (+/-)-deguelin via a key 6-endo hydroarylation

Org Lett. 2003 Oct 30;5(22):4053-5. doi: 10.1021/ol035419j.

Authors

Stefan J Pastine¹, Dalibor Sames

Affiliation

¹ Department of Chemistry, Columbia University, New York, New York 10027, USA.

PMID: 14572247
DOI: 10.1021/ol035419j

Abstract

[reaction: see text]. A concise total synthesis of (+/-)-deguelin was achieved with a longest linear sequence of six steps in 68% yield. A key step was the platinum-catalyzed 6-endo hydroarylation of an alkynone intermediate.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged-Ring Compounds / chemistry
Catalysis
Cyclization
Molecular Structure
Platinum Compounds / chemistry
Rotenone / analogs & derivatives*
Rotenone / chemical synthesis*
Rotenone / chemistry

Substances

Bridged-Ring Compounds
Platinum Compounds
Rotenone
platinum chloride
deguelin