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Org. Biomol. Chem., 2010, 8, 419 - 427, DOI: 10.1039/b910545j

Total synthesis of asperlicin C, circumdatin F, demethylbenzomalvin A, demethoxycircumdatin H, sclerotigenin, and other fused quinazolinones

Ming-Chung Tseng, Huei-Yun Yang and Yen-Ho Chu

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 ( 1a–f), (ii) diazepino[2,1-b]quinazolinediones ( 2a–e), and (iii) pyrazino[2,1-b]quinazolinediones ( 3a–e) with good overall isolated yields (23–43%, 37–47% and 31–56%, respectively). Among the quinazolino[3,2-a]benzodiazepinediones synthesized, 1a (sclerotigenin), 1b (circumdatin F), and 1f (asperlicin C) are natural products.

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