Synthetic studies related to mycobactins. II. Formation of mycobactin hydroxamic acid units by malonic ester synthesis

Abstract

6-(N-Hydroxy)lysine dihydrochloride and some related compounds have been synthesized by a reaction sequence involving the alkylation of sodium diethyl-phthalimidomalonate by 1,4-dibromobutane to form diethyl 5-bromo-1-phthalimido-pentane-1,l-dicarboxylate. During the transformation of this bromo compound to the corresponding nitro compound, cyclization to diethyl l-(2'-carboxybenzoyl)piperidine-2,2-dicarboxylate occurred.