Direct Amino Acid Catalyzed Asymmetric Synthesis of Polyketide Sugars

Abstract

Back to the future: In a biomimetic asymmetric synthesis of sugars (see scheme) sequential cross-aldol reactions of simple aldehydes were catalyzed by amino acids. Deoxysugars were obtained with excellent chemoselectivity and up to >99 % ee. This transformation may implicate a prebiotic catalytic pathway in which amino acids transferred their stereochemical information to carbohydrates.