Author's Organization：Faculty of Pharmaceutical Sciences, University of Tokyo, and Research Laboratory, Shionogi & Co., Ltd. Faculty of Pharmaceutical Sciences, University of Tokyo, and Research Laboratory, Shionogi & Co., Ltd.
Diazotization of decarbonylmethylmatrinamine (I) with silver nitrite in 10% hydrobromic acid yielded decarbonylmethylmatrinol (II) and the quaternary salt (III). Tosylation of matrinol (XIII) gave matridine (VIII), and reaction of (XIII) with trityl chloride gave matrine (XIV) quantitatively. The facile ring-closure of these compounds may be explained by the fact that the terminal end of the side chain is sterically very close to the nitrogen atom in ring-C.
