title: 1-Deoxy-D-xylulose: synthesis based on molybdate-catalyzed rearrangement of a branched-chain aldotetrose.
abstract: 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]
authors.affiliation: Omicron Biochemicals, Inc., 1347 North Ironwood Drive, South Bend, IN 46615-3566, USA.
authors.forename: S
authors.initials: S
authors.lastname: Zhao
authors.forename: L
authors.initials: L
authors.lastname: Petrus
authors.forename: A S
authors.initials: AS
authors.lastname: Serianni
mesh_terms: 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*
chemical_list: D013780:Tetroses; C044659:molybdate; D014996:Xylulose; C029724:1-deoxy-2-pentulose; D008982:Molybdenum