A practical synthesis of the dihydroxyethylene dipeptide isostere, (2S, 3R, 4S) 2-[(tert-butyloxycarbonyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptane, from D-isoascorbic acid

Article abstract of DOI:10.1016/S0040-4039(00)91679-4

The N-Boc dihydroxyethylene dipeptide isostere 7 and its N-Boc 3-(thiazol-4-yl)alanyl derivative 8 were synthesized, without purification of intermediates, from (4S,5R)-2,2-dimethyl-4-(2-methylpropyl)-5-hydroxymethyl-1,3-dioxolane (3b), in 24 and 32% over