Dihydroxylation of 4-substituted 1,2-dioxines: a concise route to branched erythro sugars
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Dihydroxylation of 4-substituted 1,2-dioxines : a concise route to branched erythro sugars. / Robinson, Tony V; Pedersen, Daniel Sejer; Taylor, Dennis K; Tiekink, Edward R T.
I: Journal of Organic Chemistry, Bind 74, Nr. 14, 2009, s. 5093-5096.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Dihydroxylation of 4-substituted 1,2-dioxines
T2 - a concise route to branched erythro sugars
AU - Robinson, Tony V
AU - Pedersen, Daniel Sejer
AU - Taylor, Dennis K
AU - Tiekink, Edward R T
PY - 2009
Y1 - 2009
N2 - 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.
AB - 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.
KW - Former Faculty of Pharmaceutical Sciences
U2 - 10.1021/jo900669u
DO - 10.1021/jo900669u
M3 - Journal article
C2 - 19588997
VL - 74
SP - 5093
EP - 5096
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 14
ER -
ID: 13435608