Concepedia

Total synthesis of the Fusarium toxin equisetin

Lisa T. Burke, Darren J. Dixon, Steven V. Ley, Félix Rodríguez

Organic & Biomolecular Chemistry · 2004 · 64 citations · 15 references

DOI

Concepts

Abstract

A short stereoselective synthesis of the Fusarium toxin equisetin, a potent inhibitor of HIV-1 integrase enzyme is described, using as the key step a stereoselective intramolecular Diels-Alder reaction of a fully conjugated E,E,E-triene with a trisubstituted gamma,delta-unsaturated beta-ketothioester.

References

15

Equisetin and a novel opposite stereochemical homolog phomasetin, two fungal metabolites as inhibitors of HIV-1 integrase

Sheo B. Singh, Deborah L. Zink, Michael Goetz et al. · Tetrahedron Letters · 1998 · 172 citations

, , +16

Equisetin biosynthesis in Fusarium heterosporum

James W. Sims, John P. Fillmore, Douglas D. Warner et al. · Chemical Communications · 2004 · 169 citations

, , +17

Further reactions of t-butyl 3-oxobutanthioate and t-butyl 4-diethyl-phosphono-3-oxobutanthioate : Carbonyl coupling reactions, amination, use in the preparation of 3-acyltetramic acids and application to the total synthesis of fuligorubin A.

Steven V. Ley, Stephen C. Smith, Peter Woodward · Tetrahedron · 1992 · 128 citations

, , +10

Antibiotic Produced by <i>Fusarium equiseti</i> NRRL 5537

H. R. Burmeister, G. A. Bennett, R. F. Vesonder et al. · Antimicrobial Agents and Chemotherapy · 1974 · 105 citations · Full text

, , +8

Equisetin, an antibiotic from Fusarium equiseti NRRL 5537, identified as a derivative of N-methyl-2,4-pyrollidone.

R. F. Vesonder, Larry W. Tjarks, W. K. Rohwedder et al. · The Journal of Antibiotics · 1979 · 90 citations · Full text

, , +4