52425-88-4Relevant academic research and scientific papers
From berbines to protopines: Regiocontrolled Hofmann elimination/ hydroboration/oxidation of N-substituted berbinium salts
Valpuesta, Maria,Diaz, Amelia,Suau, Rafael,Torres, Gregorio
, p. 964 - 971 (2006)
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, 2006.
Regio- and stereoselective stevens rearrangement of benzyltetrahydroprotoberberinium salts
Valpuesta, Maria,Diaz, Amelia,Suau, Rafael,Torres, Gregorio
, p. 4313 - 4318 (2007/10/03)
8-(Arylmethyl)berbines are conveniently obtained through a Stevens rearrangement of the corresponding N-arylmethylberbinium salts with sodium methylsulfinylmethylide in DMSO. This procedure has provided two new nonnatural 8-benzylcanadines stereoselectively, without competition from the Hofmann elimination. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
