Tetrahedron

A facile approach to trans-4, 5-pyrrolidine lactam and application in the synthesis of nemonapride and streptopyrrolidine

W Huang, JY Ma, M Yuan, LF Xu, BG Wei

Index: Huang, Wei; Ma, Jing-Yi; Yuan, Mu; Xu, Long-Fei; Wei, Bang-Guo Tetrahedron, 2011 , vol. 67, # 40 p. 7829 - 7837

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Citation Number: 15

Abstract

An efficient approach to trans-4-hydroxylpyrrolidine lactams 1 starting from amino acid is described. The utility of this method has been demonstrated in the synthesis of antipsychotic nemonapride 3 and antiangiogenic streptopyrrolidine 4. Compared four synthetic stereoisomers of natural streptopyrrolidine 4 in term of spectroscopic and physical data, the absolute structure of the natural product was proposed as (4S, 5S)-configuration.

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