Literature DB >> 19950885

Enantioselective total synthesis of (-)-(S)-stepholidine.

Jian-Jun Cheng1, Yu-She Yang.   

Abstract

Enantioselective total synthesis of (-)-(S)-stepholidine, a drug candidate for the treatment of schizophrenia and/or drug abuse, is described. Asymmetric transfer hydrogenation of imines with use of Noyori's catalyst was used as the key step and (-)-(S)-stepholidine was synthesized in 6 steps, with 42% overall yield and >99% ee.

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Year:  2009        PMID： 19950885     DOI： 10.1021/jo9020826

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  An alternative synthesis and x-ray crystallographic confirmation of (-)-stepholidine.

Authors:  Satishkumar V Gadhiya; Chunhua Hu; Wayne W Harding
Journal:  Tetrahedron Lett       Date:  2016-05-11       Impact factor: 2.415

2.  Intramolecular Redox-Mannich Reactions: Facile Access to the Tetrahydroprotoberberine Core.

Authors:  Longle Ma; Daniel Seidel
Journal:  Chemistry       Date:  2015-07-28       Impact factor: 5.236

3.  Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids.

Authors:  Joerg H Schrittwieser; Verena Resch; Silvia Wallner; Wolf-Dieter Lienhart; Johann H Sattler; Jasmin Resch; Peter Macheroux; Wolfgang Kroutil
Journal:  J Org Chem       Date:  2011-07-19       Impact factor: 4.354

Review 4.  Opportunities offered by chiral η⁶-arene/N-arylsulfonyl-diamine-RuII catalysts in the asymmetric transfer hydrogenation of ketones and imines.

Authors:  Jiří Václavík; Petr Kačer; Marek Kuzma; Libor Cervený
Journal:  Molecules       Date:  2011-06-28       Impact factor: 4.411

5.  Synthesis and Inhibition Evaluation of New Benzyltetrahydroprotoberberine Alkaloids Designed as Acetylcholinesterase Inhibitors.

Authors:  Bruna R de Lima; Juliana M Lima; Jéssica B Maciel; Carolina Q Valentim; Rita de Cássia S Nunomura; Emerson S Lima; Hector H F Koolen; Afonso Duarte L de Souza; Maria Lúcia B Pinheiro; Quezia B Cass; Felipe Moura A da Silva
Journal:  Front Chem       Date:  2019-09-18       Impact factor: 5.221

6.  Design, synthesis, and biological evaluation of novel tetrahydroprotoberberine derivatives (THPBs) as proprotein convertase subtilisin/kexin type 9 (PCSK9) modulators for the treatment of hyperlipidemia.

Authors:  Chenglin Wu; Cong Xi; Junhua Tong; Jing Zhao; Hualiang Jiang; Jiang Wang; Yiping Wang; Hong Liu
Journal:  Acta Pharm Sin B       Date:  2019-06-25       Impact factor: 11.413
  6 in total

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