Method for synthesizing optically pure glabridin

Abstract

The invention relates to a method for synthesizing optically pure glabridin. According to the method, chiral carbon of optically pure glabridin is constructed through biological enzyme catalysis, optically pure glabridin is prepared in combination with an organic synthesis method, and the key steps are that a chiral intermediate compound III is generated by using a lipase catalysis compound II, and an important intermediate compound IV is obtained through a bromination reaction. According to the method for synthesizing optically pure glabridin, raw materials are cheap and easy to obtain, and the total yield is high.

Description

technical field [0001] The invention belongs to the fields of organic synthesis and fine chemicals, and in particular relates to a method for synthesizing optically pure glabridin. Background technique [0002] Glabridin is a kind of flavonoids, which has the functions of whitening, antibacterial, anti-allergy, anti-cancer, anti-oxidation, anti-spasm, anti-inflammatory, liver protection, free radical scavenging, and blood fat and blood pressure lowering. It is highly valued by international research and application fields such as beauty, makeup, medicine and health care, showing good development prospects (Wang Xudong et al. Fine Chemical Intermediates, 2021, 51(3), 6-9.). At present, the way to obtain glabridin in my country is mainly from the precious plant Glycyrrhiza glabra, which cannot be obtained in large quantities. In my country, Glycyrrhiza glabra mainly grows in the south of the Tianshan Mountains. The harvest of licorice is limited, which makes it very important ...

AI Technical Summary

Problems solved by technology

At present, the way to obtain glabridin in my country is mainly from the precious plant Glycyrrhiza glabra, which cannot be obtained in large quantities. In my country, Glycyrrhiza glabra mainly grows in the south of the Tianshan Mountains. The harvest of licorice is limited, which makes it very important to develop an effective chemical synthesis method for the preparation of glabridin

[0003] In 2013, Wenhua et al. (Synthetic Communications, 2014, 44, 540-546) reported a method for preparing racemic glabridin by using resorcinol as a raw material through 10 steps of reaction, and the total yield was only 14%; in 2018, the patent document CN109232603A discloses a method for preparing racemic glabridin with 7-hydroxycoumarin as the starting material through 8-step reaction, the total yield is only 20%, the key step is Suzuki coupling reaction, the required boric acid reagent and metal Palladium catalysts are expensive; in 2018, the patent document CN 108440553A disclosed a method for preparing optically pure glabridin by using metal ruthenium to catalyze isoflavone intermediates, but the patent did not provide a detailed synthesis method for the isoflavone intermediates; 2020 In 2010, the patent document CN111362961A disclosed a method for preparing R-configuration glabridin with 7-hydroxychroman-4-one as the starting material through 7-step reaction, with a total yield of 30%, and the key step needs to use To the noble metal palladium catalyst and chiral phosphine ligand, and the starting material 7-hydroxychroman-4-one is not a bulk chemical product, the price is expensive (>200,000 yuan / kg)

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