Research Progress of Total Synthesis of Polygalolides

doi:10.19894/j.issn.1000-0518.220223

Chinese Journal of Applied Chemistry ›› 2023, Vol. 40 ›› Issue (5): 615-624.DOI: 10.19894/j.issn.1000-0518.220223

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Research Progress of Total Synthesis of Polygalolides

Jia-Zheng LI¹, Shu-Zhong HE²()

^1.School of Pharmacy Guizhou University，Guiyang 550000，China
^2.State Key Laboratory of Functions and Applications of Medicinal Plants，Guizhou Medical University，Guiyang 550014，China

Received:2022-06-21 Accepted:2023-02-13 Published:2023-05-01 Online:2023-05-26
Contact: Shu-Zhong HE
About author:szhe@gzu.edu.cn
Supported by:
the Science and Technology Foundation of Guizhou Province（No.the Science and Technology Foundation of Guizhou Province-ZK［2021］General 039） and the State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University(FAMP202102K)

Abstract

Abstract:

Polygalolide A and B are two new phenolic compounds isolated from the rhizome of the medicinal plant Polygala Falax Hemsl. They have a complex tetracyclic cageframe work， including a highly oxidized cycloheptanone， three oxygen-containing heterocycles and two adjacent bridge carbon centers. This review summarizes the central tetracyclic was constructed by （5+2） cycloaddition， intramolecular （3+2） cycloaddition and intramolecular nucleophilic substitution. These lay a foundation for the study of the molecular biological activity

Key words: Polygalolide A and B, Phenolic compounds, Tetracyclic, Total synthesis

CLC Number:

O629.9

Jia-Zheng LI, Shu-Zhong HE. Research Progress of Total Synthesis of Polygalolides[J]. Chinese Journal of Applied Chemistry, 2023, 40(5): 615-624.

Figures/Tables 13

Fig.1 Chemical structures of polygalolide A （1） and B （2）［3］

Fig.2 Syntheticstrategy of polygalolides

Fig.3 The （4+3） cycloaddition reaction of alkoxylidenes developed by our research group［13］

Fig.4 Synthetic route of polygalolides［5］

Fig.5 Conjugated addition of alcohol 25 with α， β-unsaturated ester （－）-24［6］

Fig.6 Stereochemical model for the predominant formation of 26（syn）［6］

Fig.7 Snider's biomimetic synthetic route of polygalolides［7］

Fig.8 Oxabicyclo［3.2.1］ skeleton was constructed by intramolecular glycositization reaction［7］

Fig.9 Oxabicyclo［3.2.1］ skeleton was constructed by intramolecular glycositization reaction［7］

Fig.10 Synthesis of cyclization precursor 42［7］

Fig.11 Study on intramolecular glycosylation reaction and screening of conditions［7］

Fig.12 Adachi's synthetic route of polygalolide A［7］

Fig.13 Proposed synthetic route of cycloheptanone

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Research Progress of Total Synthesis of Polygalolides

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