Heterocycles

Total Synthesis of (S)-(-)-Stepholidine Using (S)-tert-Butanesulfinylimine

J Cheng, L Fu, C Ling, Y Yang

Index: Cheng, Jianjun; Fu, Liqiang; Ling, Chenyu; Yang, Yushe Heterocycles, 2010 ,  vol. 81,  # 11  p. 2581 - 2592

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Citation Number: 6

Abstract

Abstract–A new synthetic strategy of (S)-(−)-stepholidine, a promising antipsychotic drug candidate, is described. Nucleophilic addition of a laterally lithiated nitrile to a (S)-tert- butanesulfinylimine was used as the key step, which was complished in 94% de and the main isomer was isolated in 52% yield.(S)-(−)-Stepholidine was prepared after another 5 steps, with an overall yield of 18.3% and> 98% ee.