Total synthesis of asperlicin C, circumdatin F, demethylbenzomalvin A, demethoxycircumdatin H, sclerotigenin, and other fused quinazolinones
- 5 November 2009
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 8 (2), 419-427
- https://doi.org/10.1039/b910545j
Abstract
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.Keywords
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