Dihydroxylation of 4-substituted 1,2-dioxines: a concise route to branched erythro sugars
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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.
Original language | English |
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Journal | Journal of Organic Chemistry |
Volume | 74 |
Issue number | 14 |
Pages (from-to) | 5093-5096 |
ISSN | 0022-3263 |
DOIs | |
Publication status | Published - 2009 |
- Former Faculty of Pharmaceutical Sciences
Research areas
ID: 13435608