Syntheses, Structures, and Enzymic Evaluations of Conformationally Constrained, Analog Inhibitors of Carnitine Acetyltransferase:(2R, 6R)-,(2S, 6S)-,(2R, 6S)-, and ( …

G Sun, PS Savle, RD Gandour, NN Bhaird…

Index: Sun, Guobin; Savle, Prashant S.; Gandour, Richard D.; a'Bhaird, Noirin Nic; Ramsay, Rona R.; Fronczek, Frank R. Journal of Organic Chemistry, 1995 , vol. 60, # 21 p. 6688 - 6695

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Citation Number: 16

Abstract

The syntheses and structures of the four stereoisomers of 6-(carboxylatomethyl)-2- (hydroxymethyl)-2, 4, 4-trimethylmorpholinium, 1, are described. The key step in the synthetic strategy involves an intramolecular Michael addition reaction. Condensation of nonracemic 34methylamino1-2-methylpropane-l, 2-diol, 3, with methyl 4-bromo-2-butenoate followed by intramolecular Michael addition gives a mixture of two diastereomers of ...