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The enantiospecific synthesis of [5-2H]-epi-shikimic acid and of (6R) [6-2H]-, (6S) [6-2H]- and [6-2H2] shikimic acid

✍ Scribed by Lolita O. Zamir; Cong-Danh Nguyen; Shu Wen Li; Anastasia Nikolakakis; Françoise Sauriol

Publisher
John Wiley and Sons
Year
1992
Tongue
French
Weight
607 KB
Volume
31
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The enantioselective synthesis of [5‐^2^H]‐5‐epi‐shikimic acid starting from commercially available L‐shikimic acid has been accomplished in this work. The introduction of the stable isotope was facilitated by an enzymic reduction of a ketone. An interesting stereospecific enolisation was also observed during this reaction resulting in partial deuteration of the 6‐equatorial position. In addition, the enantioselective syntheses of methyl (6R) [6‐^2^H]‐, and (6__S__) [6‐^2^H] shikimate are described. The procedure is an adaptation of a reported^(1)^ enantiospecific synthesis of shikimic acid, with the inclusion of an enzymic reduction step.

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