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Synthesis 2011(11): 1804-1808  
DOI: 10.1055/s-0030-1260013
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Monoalkylation of Dimethyl Alkylidenesuccinates: Simple Approach to Dialkyl-Substituted Maleic Anhydrides Including Chaetomellic Acid A

Umesh A. Kshirsagar, Narshinha P. Argade*
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India
Fax: +91(20)25902629; e-Mail: np.argade@ncl.res.in;
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Publication History

Received 10 February 2011
Publication Date:
20 April 2011 (online)

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Abstract

Natural and nonnatural dialkylmaleic anhydrides were readily prepared from dimethyl alkylidenesuccinates by sodium hexamethyldisilazide-induced selective monoalkylation followed by base-catalyzed hydrolysis.

Key words

esters - alkylations - furans - heterocycles - maleic anhydrides

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