Asymmetric synthesis of (−)-4- epi-shikimic acid

The major cycloadduct, arising from the Diels–Alder reaction of maleic anhydride and (1 E)-(2′,3′,4′,6′-tetra- O-acetyl-β- d-glucopyranosyloxy)buta-1,3-diene, is converted into methyl 3- O-(β- d-glucopyranosyl)-4- epi-shikimate and into (−)-4- epi-shikimic acid in overall yields of 20 and 17% (based...

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Bibliographic Details
Published in:Tetrahedron letters 2000-04, Vol.41 (15), p.2691-2694
Main Authors: Pornpakakul, Surachai, Pritchard, Robin G, Stoodley, Richard J
Format: Article
Language:English
Subjects:
asymmetric synthesis
carbohydrates
Diels–Alder reactions
regioselection
shikimic acid and derivatives
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Summary:The major cycloadduct, arising from the Diels–Alder reaction of maleic anhydride and (1 E)-(2′,3′,4′,6′-tetra- O-acetyl-β- d-glucopyranosyloxy)buta-1,3-diene, is converted into methyl 3- O-(β- d-glucopyranosyl)-4- epi-shikimate and into (−)-4- epi-shikimic acid in overall yields of 20 and 17% (based on the diene).
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00225-2