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From Berbines to Protopines: Regiocontrolled Hofmann Elimination/Hydroboration/Oxidation of N ‐Substituted Berbinium Salts
Author(s) -
Valpuesta María,
Díaz Amelia,
Suau Rafael,
Torres Gregorio
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500573
Subject(s) - chemistry , hydroboration , organic chemistry , chloride , sequence (biology) , medicinal chemistry , catalysis , biochemistry
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)