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

Zbigniew J. Witczak; Raphael Mielguj

doi:10.1055/s-1996-5326

Synlett 1996; 1996(1): 108-110
DOI: 10.1055/s-1996-5326

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

Zbigniew J. Witczak^* , Raphael Mielguj

^*School of Pharmacy, Department of Pharmaceutical Sciences, University of Connecticut, 372 Fairfield Road, U-92, Storrs, Connecticut 06269-2092, U.S.A.

Abstract

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(+) 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

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