A short stereoselective total synthesis of the fusarium toxin equisetin.
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.
Burke
L T
LT
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.
Dixon
D J
DJ
Ley
S V
SV
Rodríguez
F
F
D000107:Acetylation; D005670:Fusarium / Q000737:chemistry*; D019428:HIV Integrase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D015497:HIV-1; D007202:Indicators and Reagents; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes
D019428:HIV Integrase Inhibitors; D017320:HIV Protease Inhibitors; D007202:Indicators and Reagents; D011760:Pyrrolidinones; D013764:Tetrahydronaphthalenes; C024509:equisetin