Stereoselective synthesis of dihydrohydroxystreptose, virenose and l-evalose from a common precursor derived from l-arabinose

Abstract

An expeditious total synthesis of 3-C-branched rare-sugar monosaccharides dihydrohydroxystreptose, virenose and l-evalose were achieved using l-arabinose as the only key chiral pool starting material. The developed protocol involves the selective protection of hydroxyls and highly stereoselective Grignard reaction at C-3 position of the 3-ulose intermediate.