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

Valpuesta María | Zendy; Díaz Amelia | Zendy; Suau Rafael | Zendy; Torres Gregorio | Zendy

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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)

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