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Type: Journal article
Title: Dihydroxylation of 4-substituted 1,2-dioxines: A concise route to branched erythro sugars
Author: Robinson, T.
Pedersen, D.
Taylor, D.
Tiekink, E.
Citation: Journal of Organic Chemistry, 2009; 74(14):5093-5096
Publisher: Amer Chemical Soc
Issue Date: 2009
ISSN: 0022-3263
Statement of
Tony V. Robinson, Daniel Sejer Pedersen, Dennis K. Taylor and Edward R. T. Tiekink
Abstract: The synthesis of 2-C-branched erythritol derivatives, including the plant sugar (+/-)-2-C-methylerythritol 2, was achieved through a dihydroxylation/reduction sequence on a series of 4-substituted 1,2-dioxines 3. The asymmetric dihydroxylation of 1,2-dioxines was examined, providing access to optically enriched dihydroxy 1,2-dioxanes 4. The synthesized 1,2-dioxanes were converted to other erythro sugar analogues and tetrahydrofurans through controlled cleavage of the endoperoxide linkage.
Keywords: Erythritol; Dioxins; Carbohydrates; Molecular Structure; Oxidation-Reduction; Hydroxylation; Stereoisomerism
Description: Copyright © 2009 American Chemical Society
RMID: 0020091470
DOI: 10.1021/jo900669u
Appears in Collections:Chemistry and Physics publications

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