Tetrahedron

Synthesis of a key intermediate in the diaminopimelate pathway to L-Lysine: 2, 3, 4, 5-tetrahydrodipicolinic acid

EJT Chrystal, L Couper, DJ Robins

Index: Chrystal, Ewan J. T.; Couper, Lynda; Robins, David J. Tetrahedron, 1995 , vol. 51, # 37 p. 10241 - 10252

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Citation Number: 42

Abstract

2, 3, 4, 5-Tetrahydrodipicolinic acid (3) is a key intermediate in the diaminopimelate (DAP) pathway to l-lysine (7). It was synthesized as the stable racemic potassium salt (25) from dipicolinic acid (14) by esterification, hydrogenation to the cis-diester (17), followed by elimination of p-toluenesulfinic acid from the N-toluenesulfonyl derivative (24) of dimethyl cis- piperidine-2, 6-dicarboxylate with concomitant cleavage of the ester groups.(±)-2, 3, 4, 5- ...