Tetrahedron

Synthesis of 5, 5′-dihydroxyleucine and 4-fluoro 5, 5′-dihydroxyleucine, the reduction products of 4-carboxyglutamic and 4-carboxy-4-fluoroglutamic acids

…, C Fourès, S Bory, S Falcou, M Gaudry, A Marquet

Index: Dubois, Joelle; Foures, Christine; Bory, Sonia; Falcou, Serge; Gaudry, Michel; Marquet, Andree Tetrahedron, 1991 , vol. 47, # 6 p. 1001 - 1012

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Citation Number: 30

Abstract

Schemes for the synthesis of 5-5′-dihydroxyleucine 3 and its 4-fluoro analog 7 involving the condensation of a suitable “aminoacid moiety” with 2, 2-dimethyl-5-iodomethyl-1, 3- dioxane 15D or its fluoro analog 27A were tested. The anion of the ethyl N- diphenylmethylene-glycinate 25 gave better yields of 3 than the classical anion of diethyl acetamidomalonate. This strategy could not be successfully applied to the synthesis of 7, ...