Preparation and structural elucidation of (-)-tetrahydroberberine-(+)-2, 3-di(p-toluyl) tartaric acid complex

A new (2:1) complex of (-)-13aS-tetrahydroberberine [(-)-13aS-THB] with (+)-2,3-di(p-toluyl) tartaric acid (DTTA), i.e. 5,8,13,13a-tetrahydro-9,10-dimethoxy-2,3-methylenedioxy-6H dibenzo[a,g] quinolizine-2,3-di(p-toluyl) tartaric acid [2C(20)H(20)NO(4)center dot C(20)H(18)O(8)], as well as its optical active component (-)-THB. has been obtained from the resolution process of (+/-)-THB in methanol. The structures of this complex and an enantiomer(-)-13aS-THB have been characterized by CD, IR and NMR spectroscopy as well as by X-ray single crystal diffraction. (C) 2008 Elsevier B.V. All rights reserved.