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Paper | Regular issue | Vol 81, No. 11, 2010, pp.2581-2592
Published online, 30th September, 2010
DOI: 10.3987/COM-10-12056
Total Synthesis of (S)-(-)-Stepholidine Using (S)-tert-Butanesulfinylimine

Jianjun Cheng, Liqiang Fu, Chenyu Ling, and Yushe Yang*

*State Key Laboratory of Drug Research, Shanghai Institute of Material Medica, Chinese Academy of Sciences, 555, Zuchongzhi Road, Zhangjiang High-Tech Park, Shanghai 201209, China

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.