Aldonolactones as chiral templates in the synthesis of thiolactones, 1,3-polyols and hydroxy amino acids

Abstract

The usefulness of aldonolactones as chiral templates is shown in the synthesis of varied asymmetric molecules. For example, enantiomerically pure 4-thio-D-ribono and 4-thio-L-lyxono-1,4-lactones have been respectively synthesized from D-gulono- and D-ribono-1,4-lactones. Seven carbon 1,3-polyol chains have been enantioselectively obtained from D-glycero-D-gulo-heptono-1,4-lactone via chiral furanone derivatives. Also, furanones and pyranones derived from D-glucosaminic acid were employed as intermediates in the synthesis of hydroxy amino acids, such as cis-4-hydroxypipecolic acid and (2S,4S,5R)-4,5,6-trihydroxynorleucine.