Literature DB >> 17867705

Aza-Prins-pinacol approach to 7-azabicyclo[2.2.1]heptanes: syntheses of (+/-)-epibatidine and (+/-)-epiboxidine.

Alan Armstrong1, Yunas Bhonoah, Stephen E Shanahan.   

Abstract

The syntheses of (+/-)-epibatidine and (+/-)-epiboxidine have been accomplished from commercial 2-methoxy-3,4-dihydro-2H-pyran. A recently developed aza-Prins-pinacol rearrangement was employed for the construction of the key 7-azabicyclo[2.2.1]heptane skeleton of these targets.

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Year:  2007        PMID： 17867705     DOI： 10.1021/jo701536a

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


  6 in total

1.  Molecular Rearrangements in the Construction of Complex Molecules.

Authors:  Larry E Overman
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

2.  An aza-Prins cyclization approach to functionalized indolizidines from 2-allylpyrrolidines.

Authors:  Xiaoxi Liu; Michael P McCormack; Stephen P Waters
Journal:  Org Lett       Date:  2012-10-25       Impact factor: 6.005

3.  Decarboxylative Halogenation of Organic Compounds.

Authors:  Andrii Varenikov; Evgeny Shapiro; Mark Gandelman
Journal:  Chem Rev       Date:  2020-11-17       Impact factor: 60.622

4.  Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles.

Authors:  Guillaume G Launay; Alexandra M Z Slawin; David O'Hagan
Journal:  Beilstein J Org Chem       Date:  2010-04-26       Impact factor: 2.883

5.  Computational analysis of the binding ability of heterocyclic and conformationally constrained epibatidine analogs in the neuronal nicotinic acetylcholine receptor.

Authors:  Elena Soriano; José Marco-Contelles; Inés Colmena; Luis Gandía
Journal:  Mol Divers       Date:  2009-05-29       Impact factor: 2.943

Review 6.  Total synthesis of natural products using hypervalent iodine reagents.

Authors:  Gaëtan Maertens; Chloé L'Homme; Sylvain Canesi
Journal:  Front Chem       Date:  2015-01-05       Impact factor: 5.221
  6 in total

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