The First Total Synthesis of (±)-Methyl Salvianolate A Using a Convergent Strategy

被引：3

作者：

Wang, Bo ^{[1
]}

Wang, Liping ^{[2
]}

Peng, Ying ^{[2
]}

Pang, Yiying ^{[2
]}

Xiao, Hesheng ^{[2
]}

Wang, Xiaoji ^{[2
]}

Huang, Shuangping ^{[3
,4
]}

机构：

[1] Jiangxi Sci & Technol Normal Univ, Sch Chem & Chem Engn, Nanchang 330013, Jiangxi, Peoples R China

[2] Jiangxi Sci & Technol Normal Univ, Sch Life Sci, Nanchang 330013, Jiangxi, Peoples R China

[3] Jiangxi Sci & Technol Normal Univ, Sch Pharm, Nanchang 330013, Jiangxi, Peoples R China

[4] Taiyuan Univ Technol, Coll Biomed Engn, Taiyuan 030024, Shanxi, Peoples R China

来源：

MOLECULES | 2019年 / 24卷 / 05期

基金：

美国国家科学基金会;

关键词：

methyl salvianolate A; Danshen; total synthesis; Horner-Wadsworth-Emmons reaction; silyl protecting group; SELECTIVE DEPROTECTION; ACID-A;

D O I：

10.3390/molecules24050999

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Herein, a convergent, practicable and first total synthesis of the natural product, (+/-)-methyl salvianolate A, is reported. The key features of the approach are the use of a Horner-Wadsworth-Emmons reaction and the protection of multiple hydroxyls using silyl protecting groups. The employment of the readily removable silyl protecting groups allows the synthesis of (+/-)-methyl salvianolate A and its derivatives on a reasonably large scale.

引用

页数：11

共 22 条

[11] A mild, efficient and selective deprotection of t-butyldimethylsilyl-protected phenols using cesium carbonate [J].

Jiang, ZY ;

Wang, YG .

TETRAHEDRON LETTERS, 2003, 44 (19) :3859-3861

[12] Transformation of Salvianolic Acid B to Salvianolic Acid A in Aqueous Solution and the In Vitro Liver Protective Effect of the Main Products [J].

Kan, Shidong ;

Chen, Zhouzhou ;

Shao, Lei ;

Li, Ji'an .

JOURNAL OF FOOD SCIENCE, 2014, 79 (04) :C499-C504

[13] SALVIANOLIC ACID-A, A NEW DEPSIDE FROM ROOTS OF SALVIA-MILTIORRHIZA [J].

LI, LN ;

RUI, T ;

CHEN, WM .

PLANTA MEDICA, 1984, 50 (03) :227-228

[14] Effects of salvianolic acid a on oxygen radicals released by rat neutrophils and on neutrophil function [J].

Lin, TJ ;

Zhang, KJ ;

Liu, GT .

BIOCHEMICAL PHARMACOLOGY, 1996, 51 (09) :1237-1241

[15] PROTECTIVE ACTION OF 7 NATURAL PHENOLIC-COMPOUNDS AGAINST PEROXIDATIVE DAMAGE TO BIOMEMBRANES [J].

LIU, GT ;

ZHANG, TM ;

WANG, BE ;

WANG, YW .

BIOCHEMICAL PHARMACOLOGY, 1992, 43 (02) :147-152

[16] Effects of salvianolic acids on oxidative stress and hepatic fibrosis in rats [J].

Tsai, Ming-Kuei ;

Lin, Yun-Lian ;

Huang, Yi-Tsau .

TOXICOLOGY AND APPLIED PHARMACOLOGY, 2010, 242 (02) :155-164

[17] Cardioprotective effect of salvianolic acid A on isoproterenol-induced myocardial infarction in rats [J].

Wang, Shou-bao ;

Tian, Shuo ;

Yang, Fan ;

Yang, Hai-guang ;

Yang, Xiu-ying ;

Du, Guan-hua .

EUROPEAN JOURNAL OF PHARMACOLOGY, 2009, 615 (1-3) :125-132

[18] Effect of salvianic acid A on lipid peroxidation and membrane permeability in mitochondria [J].

Wang, XJ ;

Wang, ZB ;

Xu, JX .

JOURNAL OF ETHNOPHARMACOLOGY, 2005, 97 (03) :441-445

[19] Synthesis of (+)-salvianolic acid A from sodium Danshensu [J].

Xu, Kai ;

Liu, Hao ;

Liu, Delong ;

Sheng, Cheng ;

Shen, Jiefeng ;

Zhang, Wanbin .

TETRAHEDRON, 2018, 74 (40) :5996-6002

[20] Three new derivatives of anti-HIV-1 polyphenols isolated from Salvia yunnanensis [J].

Zhang, Zheng-Fu ;

Peng, Zong-Gen ;

Gao, Lei ;

Dong, Biao ;

Li, Jian-Rui ;

Li, Zhuo-Yong ;

Chen, Hong-Shan .

JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2008, 10 (05) :391-396

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