Literature DB >> 17371038

Ether-directed, stereoselective aza-Claisen rearrangements: synthesis of the piperidine alkaloid, alpha-conhydrine.

Andrew G Jamieson1, Andrew Sutherland.   

Abstract

[reaction: see text] A new approach for the stereoselective synthesis of the piperidine alkaloid (+)-alpha-conhydrine and its pyrrolidine derivative has been developed using a palladium(II)-catalyzed, MOM-ether-directed aza-Claisen rearrangement and ring-closing metathesis to effect the key steps.

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Year:  2007        PMID: 17371038     DOI: 10.1021/ol070424z

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


  2 in total

1.  Asymmetric, organocatalytic, three-step synthesis of gamma-hydroxy-(E)-alpha,beta-unsaturated sulfones and esters.

Authors:  Kimberly S Petersen; Gary H Posner
Journal:  Org Lett       Date:  2008-09-24       Impact factor: 6.005

2.  Preparation of anti-vicinal amino alcohols: asymmetric synthesis of D-erythro-sphinganine, (+)-spisulosine, and D-ribo-phytosphingosine.

Authors:  Ewen D D Calder; Ahmed M Zaed; Andrew Sutherland
Journal:  J Org Chem       Date:  2013-07-03       Impact factor: 4.354

  2 in total

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