Synthesis 2001(5): 0702-0704
DOI: 10.1055/s-2001-12778
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

A Facile Synthesis of a (±)-2,3-Disubstituted Maleic Anhydride Segment of Tautomycin [1]

Anil M. Deshpande, Arvind A. Natu, Narshinha P. Argade*
Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India
Fax: +91(20)5893153; e-Mail: argade@dalton.ncl.res.in;
Further Information

Publication History

Received 2 December 2000
Publication Date:
15 October 2004 (online)

Abstract

A convenient method for construction of a (±)-2,3-disubstituted maleic anhydride segment of antibiotic tautomycin is reported. The key steps involved in the synthesis are chemoselective condensation of diethyl malonate with 2-(bromomethyl)-3-methylmaleic anhydride (3) and regioselective NBS-bromination of the maleic anhydride derivative 7.

1

NCL Communication No. 6605.

1

NCL Communication No. 6605.