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Production and Synthetic Modifications of Shikimic Acid

Research output: Contribution to journalReview ArticleScientificpeer-review

Details

Original languageEnglish
Pages (from-to)10458-10550
Number of pages93
JournalChemical Reviews
Volume118
Issue number20
DOIs
Publication statusPublished - 24 Oct 2018
Publication typeA2 Review article in a scientific journal

Abstract

Shikimic acid is a natural product of industrial importance utilized as a precursor of the antiviral Tamiflu. It is nowadays produced in multihundred ton amounts from the extraction of star anise (Illicium verum) or by fermentation processes. Apart from the production of Tamiflu, shikimic acid has gathered particular notoriety as its useful carbon backbone and inherent chirality provide extensive use as a versatile chiral precursor in organic synthesis. This review provides an overview of the main synthetic and microbial methods for production of shikimic acid and highlights selected methods for isolation from available plant sources. Furthermore, we have attempted to demonstrate the synthetic utility of shikimic acid by covering the most important synthetic modifications and related applications, namely, synthesis of Tamiflu and derivatives, synthetic manipulations of the main functional groups, and its use as biorenewable material and in total synthesis. Given its rich chemistry and availability, shikimic acid is undoubtedly a promising platform molecule for further exploration. Therefore, in the end, we outline some challenges and promising future directions.

Keywords

  • OSELTAMIVIR PHOSPHATE TAMIFLU, DIELS-ALDER REACTION, ESCHERICHIA-COLI STRAIN, CHINESE STAR ANISE, HIGHLY EFFICIENT SYNTHESIS, MARINE NATURAL-PRODUCT, CARBOHYDRATE PHOSPHOTRANSFERASE SYSTEM, INFLUENZA NEURAMINIDASE INHIBITOR, INTERMEDIATES POTENTIALLY USEFUL, ABUNDANT (-)-SHILDMIC ACID

Publication forum classification

Field of science, Statistics Finland