An in-depth study on ring-closing metathesis of carbohydrate-derived alpha-alkoxyacrylates: Efficient syntheses of DAH, KDO, and 2-deoxy-beta-KDO

Novel, efficient synthetic pathways to DAH, KDO, and 2-deoxy-β-KDO are described. Ring-closing metathesis (RCM) of highly functionalized α-alkoxyacrylate fragments resulted in a series of synthetically versatile oxygen heterocyclic intermediates. Further functionalization of the resulting enol ether double bond and subsequent deprotection provided the natural products in high overall yields, starting from commercially available protected sugars.