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From Berbines to Protopines: Regiocontrolled Hofmann Elimination/Hydroboration/Oxidation of N-Substituted Berbinium Salts

✍ Scribed by María Valpuesta; Amelia Díaz; Rafael Suau; Gregorio Torres


Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
170 KB
Volume
2006
Category
Article
ISSN
1434-193X

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✦ Synopsis


Abstract

An improved synthetic approach to protopines based on the sequential Hofmann elimination, hydroboration and oxidation of N‐(arylmethyl)berbinium salts has been designed. By using berberine chloride as the starting material, this sequence of reactions has provided two new nonnatural protopines, N‐benzyl‐N‐nordihydroallocriptopine and N‐(p‐methoxybenzyl)‐N‐nordihydroallocriptopine and the natural allocriptopine. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)