A Convenient Synthesis of the (+) Enantiomer of Levoglucosenone and its 5-Hydroxymethyl Analog

All articles of this category (+) Levoglucosenone, a previously unavailable (+) enantiomer of 1,6-anhydro-3,4-dideoxy-β-D- glycero -hex-3-enopyranos-2-ulose, and its 5-hydroxymethyl analog have been synthesized in six steps in 28% and 41% overall yields from the known precursor, 5-hydroxymethyl-1,6-anhydro-α-L- altro -hexopyranose 1 . (+)-levoglucosenone - 5-hydroxymethyl-(+)-levoglucosenone - reductive decarboxylation - hydrous zirconium oxide - PDC oxidation