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

Ming-Chung Tseng; Huei-Yun Yang; Yen-Ho Chu

doi:10.1039/B910545J

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Organic & Biomolecular Chemistry

Issue 2, 2010

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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

Org. Biomol. Chem., 2010, 8, 419-427

DOI: 10.1039/B910545J
Received 29 May 2009, Accepted 29 Sep 2009
First published on the web 05 Nov 2009

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Abstract
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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.

Abstract from Natural Product Updates 2010

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Supplementary Info

Experimental procedures; complete ¹H and ¹³C NMR spectra of all compounds 1a–f, 2a–e, and 3a–e
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Organic & Biomolecular Chemistry

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

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