Tin triflate-mediated total synthesis of circumdatin F, sclerotigenin, asperlicin C, and other quinazolino[3,2-a][1,4]benzodiazepines.
Using tin triflate, as an effective Lewis acid, and microwaves, direct double cyclizations of bis(anthranilate)-containing tripeptide precursors to afford the total syntheses of 7-substituted quinazolino[3,2-a][1,4]benzodiazepinediones (1a-f), including natural products circumdatin F (1a), sclerotigenin (1b), and asperlicin C (1c), were achieved with good overall isolated yields (23-62%).
Tseng
Ming-Chung
MC
Department of Chemistry and Biochemistry, National Chung Cheng University, 168 University Road, Chia-Yi, Taiwan 621, ROC.
Lai
Chi-Yu
CY
Chu
Yu-Wan
YW
Chu
Yen-Ho
YH
D000470:Alkaloids / Q000138:chemical synthesis*; D001569:Benzodiazepines / Q000138:chemical synthesis*; D001570:Benzodiazepinones / Q000138:chemical synthesis*; D014001:Tin / Q000737:chemistry*
D000470:Alkaloids; D001570:Benzodiazepinones; C428194:circumdatin F; C539066:sclerotigenin; D001569:Benzodiazepines; D014001:Tin; C057101:asperlicin C