Syntheses of 6-oxodecahydroisoquinoline-3-carboxylates. Useful intermediates for the preparation of conformationally defined excitatory amino acid antagonists

PL Ornstein, MB Arnold, NK Augenstein…

Index: Ornstein; Arnold; Augenstein; Paschal Journal of Organic Chemistry, 1991 , vol. 56, # 14 p. 4388 - 4392

Full Text: HTML

Citation Number: 44

Abstract

We have prepared three of the four possible diastereomers of ethyl 6-oxo-2- (methoxycarbonyl) decahydroisoquinoline-3-carboxylic acid (two cis-ring and one trans ring juncture ketones, 3a-c) by a convergent route from (&)-m-tyrosine. These ketones are useful intermediates for the preparation of conformationally constrained acidic amino acids as N- methyl-D-aspartic acid (NMDA) receptor antagonists, eg, LY274614 and LY233536 (1 and ...