An Efficient Approach to the Synthesis of Ethyl Esters of 2,6-Anhydro-3-Deoxy-D-Gluco And D-Allo-Heptanoates

Abstract

ABSTRACT An efficient synthesis of analogues of DAH (3-deoxy-D-arabino-hept-2-ulosonic acid) and DRH (3-deoxy-D-ribo-hept-2-ulosonic acid) is described. The route exploits a previously published highly double-stereoselective hetero Diels-Alder reaction catalyzed by a chiral salenCo(II) complex. Asymmetric dihydroxylation followed by selective reduction leads to stereoselective introduction of hydroxy groups at C-4 and C-5. Oxidative cleavage of the C-6 side-chain, in situ reduction of the resulting aldehyde and deprotection afford the desired targets, which may be useful precursors to the simple analogues of the anti-influenza agent GG167.