TOTAL SYNTHESIS OF (S)-(-)-STEPHOLIDINE USING (S)-TERT-BUTANESULFINYLIMINE

A new synthetic strategy of (S)-()-stepholidine, a promising antipsychotic drug candidate, is described. Nucleophilic addition of a laterally lithiated nitrile to a (5)-tert-butanesulfinylimine was used as the key step, which was complished in 94 % de and the main isomer was isolated in 52% yield. (...

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Bibliographic Details
Published inHeterocycles Vol. 81; no. 11; pp. 2581 - 2592
Main Authors Cheng, Jianjun, Fu, Liqiang, Ling, Chenyu, Yang, Yushe
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Total Synthesis
DRUG
TERT-BUTANESULFINYL IMINES
ASYMMETRIC-SYNTHESIS
Schizophrenia
Tetrahydroprotoberberine
Sulfinylimine
Stepholidine
AGONIST
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Summary:A new synthetic strategy of (S)-()-stepholidine, a promising antipsychotic drug candidate, is described. Nucleophilic addition of a laterally lithiated nitrile to a (5)-tert-butanesulfinylimine was used as the key step, which was complished in 94 % de and the main isomer was isolated in 52% yield. (S)-(-)-St epholidine was prepared after another 5 steps, with an overall yield of 18.3% and > 98% ee.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-10-12056