Synthesis of tenuazonic acid analogues.
The synthesis of two 1.5-diaryltetramic acids, aryl analogues of tenuazonic acid, is described. The reactivity of position 4 of these tetramic acids towards primary and secondary amines, and o-methylation led to the synthesis of 4-substituted-delta3-pyrroline-2-one. Further, reactivity of position 3 has been indicated by the formation of 3-arylidenepyrrolidine-2.4-diones and by diazo-coupling. The structures assigned to the new compounds are substantiated by IR and NMR data.
D000903:Antibiotics, Antineoplastic / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared / Q000379:methods; D013720:Tenuazonic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D000903:Antibiotics, Antineoplastic; D007202:Indicators and Reagents; D013720:Tenuazonic Acid