Literature DB >> 11429891

Enantioselective construction of cyclic quaternary centers: (-)-mesembrine.

D F Taber1, T D Neubert.   

Abstract

The preparation of the crystalline amide 2 is reported. Conjugate addition to 2 proceeded with the expected high diastereocontrol to give 3. This set the stage for subsequent intramolecular alkylidene C-H insertion to give, after ozonolysis and aldol condensation, (-)-mesembrine 1. Amide 2 should be a useful chiron for the enantioselective construction of cyclic quaternary centers.

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Year:  2001        PMID: 11429891     DOI: 10.1021/jo001237g

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


  3 in total

1.  Opening of aryl-substituted epoxides to form quaternary stereogenic centers: synthesis of (-)-mesembrine.

Authors:  Douglass F Taber; Yigang He
Journal:  J Org Chem       Date:  2005-09-16       Impact factor: 4.354

Review 2.  Chemical and biological aspects of Narcissus alkaloids.

Authors:  Jaume Bastida; Rodolfo Lavilla; Francesc Viladomat
Journal:  Alkaloids Chem Biol       Date:  2006

3.  Enantioselective synthesis of (+)-majusculone.

Authors:  Douglass F Taber; M Inthikhab Sikkander; Pierre H Storck
Journal:  J Org Chem       Date:  2007-04-21       Impact factor: 4.354

  3 in total

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