Issue 21, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of the necine base (−)-supinidine from (S )-glutamic acid

Carole M. Boynton,a   Alan T. Hewson*a  and  Douglas Mitchella  

* Corresponding authors

a Division of Chemistry and Biomedical Research Centre, Sheffield Hallam University, Pond Street, Sheffield, UK

Abstract

A route is described towards the pyrrolizidine nucleus from derivatives of 5-acetylpyrrolidin-2-one using an intramolecular Wittig reaction with vinylphosphonium salts. The acetoxy ketone 15, derived from (S )-N-benzyloxycarbonylpyroglutamic acid, affords 16, a known precursor of (−)-supinidine.

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Article information

DOI
https://doi.org/10.1039/B005516F
Article type
Paper
Submitted
10 Jul 2000
Accepted
04 Sep 2000
First published
19 Oct 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3599-3602

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Synthesis of the necine base (−)-supinidine from (S )-glutamic acid

C. M. Boynton, A. T. Hewson and D. Mitchell, J. Chem. Soc., Perkin Trans. 1, 2000, 3599 DOI: 10.1039/B005516F

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