First Total Synthesis of Deinococcucin A, a Key Glycolipid Found in Cell Membranes of Extremophilic Bacteria.

Deinococcucin A is a secondary metabolite isolated from a gut bacteria of carpenter ant, member of extremophilic Deinoccocus family. The structure is a glycolipid containing N-acetyl glucosamine, linked in α anomeric position to a chiral 2,3-dihydroxypropanamide moiety. We succeeded a new strategy starting directly from N-acetylglucosamine and transforming in an efficient manner an allyl group to the corresponding chiral α-hydroxyamide. Three key steps were used: the oxidation of primary amine to nitrile using TCCA, as well as its hydrolysis to the corresponding amide using palladium (II) catalyzed conditions. The synthesis was completed in only 10 steps with an overall yield of 3%.