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

✍ Scribed by Surachai Pornpakakul; Robin G Pritchard; Richard J Stoodley

Book ID: 104210093
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 154 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00225-2

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✦ Synopsis

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

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