Synthesis of (+)-salvianolic acid A from sodium Danshensu

被引：12

作者：

Xu, Kai ^{[1
]}

Liu, Hao ^{[1
]}

Liu, Delong ^{[1
]}

Sheng, Cheng ^{[2
]}

Shen, Jiefeng ^{[1
]}

Zhang, Wanbin ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

[2] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

来源：

TETRAHEDRON | 2018年 / 74卷 / 40期

基金：

中国国家自然科学基金;

关键词：

Salvianolic acid A; ortho-Vanillin; Sodium Danshensu; Asymmetric catalysis; Deprotection; CATALYZED ALLYLIC ALKYLATION; ALPHA-AMINO-ACIDS; PD/CU DUAL CATALYSIS; ASYMMETRIC HYDROGENATION; SALVIANOLIC ACID; ALCOHOLS; KETONES; BETA; STEREOCENTERS; CONSTRUCTION;

D O I：

10.1016/j.tet.2018.08.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-Salvianolic acid A, one of the most active components in the traditional Chinese medicine Danshen, has been synthesized over 10 steps in 6.5% overall yield. Starting from inexpensive ortho-vanillin and sodium Danshensu (synthesized via asymmetric catalysis in our group), the process consists of the following: A Wittig reaction that gives the desire product with absolute E-configuration, a demethylation reaction with AlCl3 in a satisfactory yield, and a practical deprotection of allylic groups to afford the terminal product (+)-salvianolic acid A. The current synthetic technology possesses the advantages of using inexpensive starting materials, mild reaction conditions and has the potential for use in large scale synthesis. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：5996 / 6002

页数：7

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