Issue 18, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

The first stereospecific synthesis of l-tetrahydrodipicolinic acid†; a key intermediate of diaminopimelate metabolism

Jennifer F. Caplan,a   Andrew Sutherlanda  and  John C. Vederas*a  

* Corresponding authors

a Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada
E-mail: john.vederas@ualberta.ca

Abstract

L-Tetrahydrodipicolinic acid 1, a key intermediate of diaminopimelate metabolism has been prepared in 6 steps and 23% overall yield from L-allylglycine 4. The key step during this synthesis involves a base mediated cyclisation of dimethyl (2RS,6S)-2-[N-(benzyloxycarbonyl)-N-(p-tolylsulfonyl)amino]-6-[N-(benzyloxycarbonyl)amino]heptane-1,7-dioate 8 to give (2S)-N-(benzyloxycarbonyl)-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid 9. 1H NMR studies show this one pot transformation involves four steps; base elimination of toluene-p-sulfinic acid, intramolecular nucleophilic attack of the 6-benzyloxycarbonylamino group on the resulting imine, followed by hydrolysis of the esters and elimination of benzyl carbamate under acidic work-up to give the cyclic enamine 9.

Graphical abstract: The first stereospecific synthesis of l-tetrahydrodipicolinic acid; a key intermediate of diaminopimelate metabolism

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Article information

DOI
https://doi.org/10.1039/B105091P
Article type
Paper
Submitted
11 Jun 2001
Accepted
25 Jul 2001
First published
23 Aug 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2217-2220

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The first stereospecific synthesis of L-tetrahydrodipicolinic acid; a key intermediate of diaminopimelate metabolism

J. F. Caplan, A. Sutherland and J. C. Vederas, J. Chem. Soc., Perkin Trans. 1, 2001, 2217 DOI: 10.1039/B105091P

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