Literature DB >> 16869657

Six-step synthesis of (S)-brevicolline from (S)-nicotine.

Florence F Wagner1, Daniel L Comins.   

Abstract

[reaction: see text] A six-step synthesis of (S)-brevicolline from (S)-nicotine is reported. Regioselective trisubstitution of the pyridine ring of nicotine, followed by successive Suzuki cross-coupling and Buchwald amination reactions, afforded the enantiopure beta-carboline alkaloid, brevicolline.

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Year:  2006        PMID： 16869657     DOI： 10.1021/ol061334h

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


  3 in total

1.  Phenological changes in the concentration of alkaloids of Carex brevicollis in an Alpine rangeland.

Authors:  Juan Busqué; Mercedes Martin Pedrosa; Blanca Cabellos; Mercedes Muzquiz
Journal:  J Chem Ecol       Date:  2010-10-05       Impact factor: 2.626

2.  o-(Trialkylstannyl)anilines and Their Utility in Stille Cross-Coupling: Direct Introduction of the 2-Aminophenyl Substituent.

Authors:  Enver Cagri Izgu; Thomas R Hoye
Journal:  Tetrahedron Lett       Date:  2012-09-12       Impact factor: 2.415

3.  Site-selective Suzuki-Miyaura coupling of heteroaryl halides - understanding the trends for pharmaceutically important classes.

Authors:  Joshua Almond-Thynne; David C Blakemore; David C Pryde; Alan C Spivey
Journal:  Chem Sci       Date:  2016-08-09       Impact factor: 9.825
  3 in total

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