Dihydroxylation of 4-substituted 1,2-dioxines: a concise route to branched erythro sugars.
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.
Robinson
Tony V
TV
Department of Chemistry, The University of Adelaide, South Australia 5005, Australia.
Pedersen
Daniel Sejer
DS
Taylor
Dennis K
DK
Tiekink
Edward R T
ER
D002241:Carbohydrates / Q000737:chemistry*; D004147:Dioxins / Q000737:chemistry*; D004896:Erythritol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006900:Hydroxylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D002241:Carbohydrates; D004147:Dioxins; C043904:3-C-methylerythritol; D004896:Erythritol