Dihydroxylation of 4-substituted 1, 2-dioxines: A concise route to branched erythro sugars

TV Robinson, DS Pedersen, DK Taylor…

Index: Robinson, Tony V.; Pedersen, Daniel Sejer; Taylor, Dennis K.; Tiekink, Edward R. T. Journal of Organic Chemistry, 2009 , vol. 74, # 14 p. 5093 - 5096

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Citation Number: 16

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 ...