1-Deoxy-D-xylulose: synthesis based on molybdate-catalyzed rearrangement of a branched-chain aldotetrose.
1-Deoxy-D-xylulose has been prepared in seven steps and approximately 21% overall yield from 2,3-O-isopropylidene-D-erythrono-1,4-lactone. The key reaction 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, suggesting routes to protected 2-ketoses and alpha-ketoacids/esters. This synthetic route mimics reactions of the non-mevalonate isoprenoid pathway in plants and bacteria. [reaction: see text]
Zhao
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Omicron Biochemicals, Inc., 1347 North Ironwood Drive, South Bend, IN 46615-3566, USA.
Petrus
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Serianni
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D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008982:Molybdenum / Q000737:chemistry*; D013780:Tetroses / Q000737:chemistry*; D014996:Xylulose / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D013780:Tetroses; C044659:molybdate; D014996:Xylulose; C029724:1-deoxy-2-pentulose; D008982:Molybdenum