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Synthesis 2011(17): 2838-2842  
DOI: 10.1055/s-0030-1260140
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Intramolecular Chemoselective Acylation of a Suitably Substituted Isoindole: Synthesis of (±)-Chilenine and (±)-Deoxychilenine

Prasad B. Wakchaure, 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 14 May 2011
Publication Date:
27 July 2011 (online)

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Abstract

Starting from 3,4-dimethoxyhomophthalic anhydride and 6-bromohomopiperonylamine, concise and efficient syntheses of Chilean berberis products chilenine and deoxychilenine have been demonstrated via partially divergent routes by taking advantage of facile air-oxidation of homophthalimide along with intramolecular chemoselective acylation as the key steps.

Key words

homophthalic anhydride - isoindole - chemoselective acylation - chilenine - deoxychilenine - total synthesis

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