TRANSFORMATION OF PROTOBERBERINES INTO SPIROBENZYLISOQUINOLINES. STEREOSELECTIVE CONVERSION OF COPTISINE INTO (±)-OCHROBIRINE

Miyoji Hanaoka; Shunichiro Sakurai; Takeshi Ohshima; Shingo Yasuda; Chisato Mukai

doi:10.1248/cpb.30.3446

Chemical and Pharmaceutical Bulletin

Online ISSN : 1347-5223
Print ISSN : 0009-2363

TRANSFORMATION OF PROTOBERBERINES INTO SPIROBENZYLISOQUINOLINES. STEREOSELECTIVE CONVERSION OF COPTISINE INTO (±)-OCHROBIRINE

Miyoji Hanaoka, Shunichiro Sakurai, Takeshi Ohshima, Shingo Yasuda, Chisato Mukai

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Keywords: stereoselective transformation

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Volume 30 (1982) Issue 9 Pages 3446-3449

DOI https://doi.org/10.1248/cpb.30.3446

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Abstract

Reduction of the 8, 14-cycloberbin-13-one (7a), derived from coptisine (6a), with LiAlH (OBu^t)₃ gave stereoselectively the alcohol (8a) which was subsequently treated with ethyl chloroformate to afford the oxazolidinone (10a). Hydrolysis of 10a followed by methylation with methyl iodide provided (±)-ochrobirine (1a).

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