Total synthesis of asperlicin C, circumdatin F, demethylbenzomalvin A, demethoxycircumdatin H, sclerotigenin, and other fused quinazolinones.
Using scandium triflate and microwaves, the direct double dehydrocyclization of anthranilate-containing tripeptides was achieved, affording the total syntheses of (i) quinazolino[3,2-a]benzodiazepinediones (), (ii) diazepino[2,1-b]quinazolinediones (), and (iii) pyrazino[2,1-b]quinazolinediones () with good overall isolated yields (23-43%, 37-47% and 31-56%, respectively). Among the quinazolino[3,2-a]benzodiazepinediones synthesized, (sclerotigenin), (circumdatin F), and (asperlicin C) are natural products.
Tseng
Ming-Chung
MC
Institute of Molecular Biology, Academia Sinica, Nankang, Taipei, Taiwan, ROC.
Yang
Huei-Yun
HY
Chu
Yen-Ho
YH
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D001570:Benzodiazepinones / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D052999:Quinazolinones / Q000138:chemical synthesis* / Q000737:chemistry*
D000470:Alkaloids; D001570:Benzodiazepinones; D052999:Quinazolinones; C428194:circumdatin F; C547945:demethoxycircumdatin H; C547944:demethylbenzomalvin A; C539066:sclerotigenin; C057101:asperlicin C