Divergent Cycloaddition and Ring-Closing Metathesis Approaches to Indolizidine and Pyrrolo[1,2-a]azepine Skeletons from a Chiral Precursor: An Expeditious Route to (-)-8-epi-Swainsonine Triacetate

Nath, Madhumita and Mukhopadhyay, Ranjan and Bhattacharjya, Anup (2006) Divergent Cycloaddition and Ring-Closing Metathesis Approaches to Indolizidine and Pyrrolo[1,2-a]azepine Skeletons from a Chiral Precursor: An Expeditious Route to (-)-8-epi-Swainsonine Triacetate. Organic Letters, 8 (2). pp. 317-320.

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    Abstract

    A divergent strategy for the synthesis of diverse azabicyclic ring systems has been developed in which a chiral N-allylpyrrolidine derivative, obtained from a carbohydrate precursor was converted to (-)-8-epi-swainsonine triacetate by RCM and to a pyrrolo[1,2-a]azepine derivative and a 3-hydroxymethyl-substituted indolizidine by N-allylcarbohydrate nitrone and nitrile oxide cycloadditions.

    Item Type: Article
    URI: http://www.eprints.iicb.res.in/id/eprint/451
    Subjects: Chemistry
    Divisions: Indian Institute of Chemical Biology
    Depositing User: Ms Sutapa Ganguly
    Date Deposited: 01 Nov 2011 16:38
    Last Modified: 03 Feb 2012 12:44
    Official URL: http://dx.doi.org/10.1021/ol052716a CCC: $33.50
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