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Synthesis 2010(4): 643-650  
DOI: 10.1055/s-0029-1218606
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

First Total Synthesis of (-)-Circumdatin H, a Novel Mitochondrial NADH Oxidase Inhibitor

D. Subhas Bose*, M. Venu Chary
Organic Chemistry Division III, Fine Chemicals Laboratory, Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India
Fax: +91(40)27160387; e-Mail: dsb@iict.res.in; e-Mail: bose_iict@yahoo.co.in;
Further Information

Publication History

Received 6 October 2009
Publication Date:
16 December 2009 (online)

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Abstract

An efficient and highly convergent synthesis of the mitochondrial NADH oxidase inhibitor (-)-circumdatin H is described. The strategy employs the intramolecular Eguchi aza-Wittig protocol as a key step to install the crucial central core BC ring system, leading to the first total synthesis of the target molecule.

Key words

benzodiazepine alkaloids - circumdatin H - mitochondrial NADH oxidase - intramolecular aza-Wittig reaction - Eguchi protocol - quinazolin-4(3H)-ones

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