78987-04-9Relevant academic research and scientific papers
Studies in Protoberberine Alkaloids: Part XIX - Synthesis of (+/-)-Thalictrifoline, (+/-)-Sinactine and (+/-)-Cavidine
Pai, B. R.,Natarajan, S.,Suguna, H.,Rajeswari, S.,Chandrasekaran, S.,Nagarajan, K.
, p. 607 - 611 (2007/10/02)
(+/-)-Thalictrifoline (14), (+/-)-sinactine (13) and (+/-)-cavidine (18) have been synthesised from trans- and cis-13-carboxy-9,10-methylenedioxy-2,3-dimethoxy-8-oxo-tetrahydroprotoberberines (8 and 9). 8 and 9 are obtained by condensing 3,4-methylenedioxyhomophthalic anhydride (6) and 6,7-dimethoxyisoquinoline (7).
Absolute Configurations of the cis- and trans-13-Methyltetrahydroprotoberberines. Total Synthesis of (+)-Thalictricavine, (+)-Canadine, (+/-)-, (-)-, and (+)-Thalictrifoline, and (+/-)-, (-)-, and (+)-Cavidine
Iwasa, Kinuko,Gupta, Yash Pal,Cushman, Mark
, p. 4744 - 4750 (2007/10/02)
The tetrahydroprotoberberine alkaloids (+)-thalictricavine and (+)-canadine have been synthesized from an optically resolved (+)-13-carboxy-7,8,13,14-tetrahydro-9-oxoprotoberberine .This establishes the absolute configuration of (+)-thalictricavine as 13S,14R. (+)-Thalictrifoline and (+)-cavidine have also been prepared from a common intermediate, (+)-32, whose absolute configuration was established by correlation with (+)-26.This determines the absolute configuration of (+)-thalictrifoline as 13R,14R, of (+)-corydalic acid methyl ester (22) as 3R,4R, and of the protopine (+)-corycavine (20) as 13R.
