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Phosgenation of benzyltetrahydroisoquinolines: A new method of berbines and berbin-8-ones synthesis

✍ Scribed by J.F. Stambach; L. Jung

Book ID
104203043
Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
402 KB
Volume
41
Category
Article
ISSN
0040-4020

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✦ Synopsis

Ahatraet-A novel synthesis of the berbine ring skeleton by the way of the berbin-8-ones is reported. Treatment of I-benzyl-1,2,3,4-tetrahydroisoquinolines la-d with phosgene gas gave a new series of Nchloroformyl derivatives 2ad. Intramolecular ring closure of these compounds in presence of a Lewis acid catalyst afforded berbin-&ones 3a-d in good yield. The choice of the cyclization catalyst is discussed. Reduction of products 3a-d with lithium aluminium hydride gave the berbines 4a-d Hydrolysis of berbines

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