Chemical synthesis of shikimic acid and its analogues

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, shikim...

Production and Synthetic Modifications of Shikimic Acid.

This contribution reviews all the synthetic work on tetrodotoxin that has appeared in the literature through June 2011.

https://www.mdpi.com/1660-3397/9/10/2046/pdf

The Chemical Synthesis of Tetrodoxin: An Ongoing Quest

This review provides a comprehensive coverage of the history, biology and chemistry of tetrodotoxin (TTX). It traces the origin of this remarkable molecule all the way back to the ancient Chinese medicine records. The discovery of biological activity, isolation, and a brief overview of structure elucidation are summarized. Next, the biology of TTX is discussed, primarily in the context of its activity in the sodium channels, its anesthetic properties, and its potential use in cancer treatment or drug addiction. Biosynthesis of TTX is covered before the discussion of the total syntheses. All total, formal or partial syntheses are covered but those total syntheses that have been discussed in previous reviews are only briefly summarized. Finally, the synthesis of natural and unnatural derivatives is surveyed, and a conclusion and outlook are provided for this very extensive field of endeavor. To the best of our knowledge the literature coverage is complete up to December 2018.

Tetrodotoxin: History, Biology, and Synthesis.

A convenient bioassay for detecting nanomolar concentrations of tetrodotoxin

Synthetic intermediates potentially useful for the synthesis of tetrodotoxin and derivatives. III. Synthesis of a key lactone intermediate from shikimic acid

Synthetic intermediates potentially useful for the synthesis of tetrodotoxin and derivatives. II. Reaction of diazomethane with some shikimic acid derivatives.

Choung U. Kim

Papers

Synthetic intermediates potentially useful for the synthesis of tetrodotoxin and derivatives. III. Synthesis of a key lactone intermediate from shikimic acid

Synthetic intermediates potentially useful for the synthesis of tetrodotoxin and derivatives. II. Reaction of diazomethane with some shikimic acid derivatives.