Literature DB >> 12153207

First enantioselective total synthesis of (-)-tejedine.

You-Chu Wang1, Paris E Georghiou.   

Abstract

[structure: see text] The first enantioselective total synthesis of (-)-tejedine (1) is reported. Tejedine is a seco-bisbenzyltetrahydroisoquinoline isolated in 1998 as a minor component from Berberis vulgaris. The synthesis was achieved using a strategy employing four key steps, including a chiral auxiliary-assisted diastereoselective Bischler-Napieralski cyclization.

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Year:  2002        PMID: 12153207     DOI: 10.1021/ol0261635

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Nantenine as an acetylcholinesterase inhibitor: SAR, enzyme kinetics and molecular modeling investigations.

Authors:  Stevan Pecic; Marie A McAnuff; Wayne W Harding
Journal:  J Enzyme Inhib Med Chem       Date:  2010-06-28       Impact factor: 5.051

2.  Optimisation of tetrahydroisoquinoline-based chimeric microtubule disruptors.

Authors:  Wolfgang Dohle; Mathew P Leese; Fabrice L Jourdan; Christopher J Chapman; Ernest Hamel; Eric Ferrandis; Barry V L Potter
Journal:  ChemMedChem       Date:  2014-05-12       Impact factor: 3.466

3.  [2,2'-Imino-diethano-lato(2-)-κO,N,O'][4-(meth-oxy-carbonyl-meth-yl)phen-yl]boron.

Authors:  Ahmed L Zein; Louise N Dawe; Paris E Georghiou
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-30

4.  (+/-)-Nantenine analogs as antagonists at human 5-HT(2A) receptors: C1 and flexible congeners.

Authors:  Sandeep Chaudhary; Stevan Pecic; Onica Legendre; Hérnan A Navarro; Wayne W Harding
Journal:  Bioorg Med Chem Lett       Date:  2009-03-16       Impact factor: 2.823

5.  Total Synthesis of the Ortho-Hydroxylated Protoberberines ( S)-Govaniadine, ( S)-Caseamine, and ( S)-Clarkeanidine via a Solvent-Directed Pictet-Spengler Reaction.

Authors:  Brendan Horst; Martin J Wanner; Steen Ingemann Jørgensen; Henk Hiemstra; Jan H van Maarseveen
Journal:  J Org Chem       Date:  2018-12-03       Impact factor: 4.354

  5 in total

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