The Modification Of Quinic Acid And Synthesis Of Its Derivatives

Quinic acid is one of the small number chiral source with multiple chiral centers, which has cyclohexane skeleton of polyhydroxy. It is also a polyhydroxy ring compound with optical properties. And in recent years,quinic acid has been a dramatic natural chiral source.This paper first reviews the pharmacological activity,pharmacological effects and preparation methods of quinic acid and two important derivatives-shikimic acid and chlorogenic acid. Then by modifying the quinic acid structure,we designed and synthesized two types of quinic acid derivatives,and characterized the products in corresponding IR,1H NMR, MS and element content analysis. The first kind of product is based on quinic acid which acted as raw materials, then make the ketal reaction to protect the adJacent hydroxyl groups, lactone reaction to protect 5 hydroxyl and dehydroxylation synthesis to get the shikimic acid intermediates: 3,4-isopropylidene-quinic acid methyl ester and 3,4-isopropylidene shikimic acid lactone. During the experiments, we explore the experimental conditions in the first step to get the optimum experimental conditions, reaction time and improve the reaction yield. Another target products are two kinds of caffeoyl quinic acid analogues by the transformation of the molecular structure of chlorogenic acid.