1-Deoxy-D-xylulose: Synthesis based on molybdate-catalyzed rearrangement of a branched-chain aldotetrose

[GRAPHICS] 1-Deoxy-D-xylulose has been prepared in seven steps and similar to 21% over all yield from 2,3-O-isopropylidene-D-erythrono-1,4-lactone. The key reacti on involves transformation of a branched-chain aldotetrose to the 1-deoxy-2 -ketopentose catalyzed by molybdic acid. Other branched-chain aldotetroses containing bulkier substituents at C2 also engage in the conversion, sugges ting routes to protected 2-ketoses and alpha -ketoacids/ esters. This synth etic route mimics reactions of the non-mevalonate isoprenoid pathway in pla nts and bacteria.