A short stereoselective total synthesis of the fusarium toxin equisetin

L T Burke; D J Dixon; S V Ley; F Rodríguez

doi:10.1021/ol006493u

A short stereoselective total synthesis of the fusarium toxin equisetin

Org Lett. 2000 Nov 16;2(23):3611-3. doi: 10.1021/ol006493u.

Authors

L T Burke¹, D J Dixon, S V Ley, F Rodríguez

Affiliation

¹ Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.

PMID: 11073657
DOI: 10.1021/ol006493u

Abstract

A short stereoselective synthesis of the fusarium toxin equisetin, an N-methylserine-derived acyl tetramic acid and potent inhibitor of HIV-1 integrase enzyme, is described using as the key step a stereoselective lithium perchlorate mediated intramolecular Diels-Alder reaction of a fully conjugated E,E,E-triene with a trisubstituted gamma,delta-unsaturated beta-ketothioester.

Publication types

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

MeSH terms

Acetylation
Fusarium / chemistry*
HIV Integrase Inhibitors / chemical synthesis*
HIV Integrase Inhibitors / chemistry
HIV Protease Inhibitors / chemical synthesis*
HIV Protease Inhibitors / chemistry
HIV-1
Indicators and Reagents
Pyrrolidinones / chemical synthesis
Pyrrolidinones / chemistry
Stereoisomerism
Tetrahydronaphthalenes*

Substances

HIV Integrase Inhibitors
HIV Protease Inhibitors
Indicators and Reagents
Pyrrolidinones
Tetrahydronaphthalenes
equisetin