A New Synthesis of dl-Vasicine and a Methoxy Analog1

PL Southwick, J Casanova Jr

Index: Southwick; Casanova Journal of the American Chemical Society, 1958 , vol. 80, p. 1168,1173

Full Text: HTML

Citation Number: 23

Abstract

Work on the chemistry of vasicine (Ia) by several groups of workersa culminated in the synthesis of the alkaloid by Spath, Kuffner and Platzer4 in 1935. The first synthesis depended on the preparation of methyl a-hydroxy-y-aminobutyrate, which was treated with o- nitrobenzyl chloride to produce a low yield (ca. 7%) of l-(o-nitrobenzyl)-3-hydroxy-2- oxopyrrolidine (IIa). Compound IIa, when treated with stannous chloride in hydrochloric ...