A simple route for synthesis of 4-phospho-d-erythronate

Abstract

4-Phospho-D-erythronate is an intermediate in synthesis of pyridoxal 5′-phosphate in some bacteria and an inhibitor of ribose 5-phosphate isomerase. Previous synthetic schemes for the preparation of 4-phospho-D-erythronate required expensive precursors and typically gave low yields. We report a straightforward synthesis of 4-phospho-D-erythronate from the inexpensive precursor D-erythronolactone in 5 steps with a preparatively useful yield of 22%.

Highly Stereocontrolled and Regiocontrolled Syntheses of 2,3,4-Trisubstituted Alkanoates and Lactones

“…Among these valuable intermediates are optically active vicinal amino alcohols, diols, amino diols, polyols such as carbohydrates, and dihydroxyfuranones . These structurally significant motifs are found in many natural products. , The value of these building blocks is enhanced even more when stereocontrolled transformations of only one or two of the several resident functionalities can be achieved selectively in good yields. We recently developed an asymmetric synthesis of densely functionalized and highly enantiomerically enriched 2,3,4-trisubstituted alkanoate esters illustrated by ester (−)- 3 (Scheme ).…”