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
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
收藏
页数:11
相关论文
共 22 条
[1]   Selective deprotection of either alkyl or aryl silyl ethers from aryl, alkyl bis-silyl ethers [J].
Ankala, SV ;
Fenteany, G .
TETRAHEDRON LETTERS, 2002, 43 (27) :4729-4732
[2]  
Chen W. Q., 2015, CN Patent, Patent No. [105085267A, 105085267]
[3]  
Chinese Pharmacopoeia Commission, 2015, PHARMACOPOEIA PEOPLE, V1, P76
[4]   Selective deprotection of silyl-protected phenols using solid NaOH and a phase transfer catalyst [J].
Crouch, RD ;
Stieff, M ;
Frie, JL ;
Cadwallader, AB ;
Bevis, DC .
TETRAHEDRON LETTERS, 1999, 40 (16) :3133-3136
[5]   The total synthesis of salvianolic acid F [J].
Dalla, V ;
Cotelle, P .
TETRAHEDRON, 1999, 55 (22) :6923-6930
[6]  
Duynstee HI, 1999, EUR J ORG CHEM, V1999, P2623
[7]   Antiplatelet and antithrombotic activities of salvianolic acid A [J].
Fan, Hua-Ying ;
Fu, Feng-Hua ;
Yang, Ming-Yan ;
Xu, Hui ;
Zhang, Ai-Hong ;
Liu, Ke .
THROMBOSIS RESEARCH, 2010, 126 (01) :E17-E22
[8]  
Huang S. P., 2017, CN Patent, Patent No. [106905154A, 106905154]
[9]   First Total Syntheses of Oresbiusins A and B, Their Antipodes, and Racemates: Configuration Revision and Anti-HIV Activity [J].
Hwu, Jih Ru ;
Varadaraju, Tirumala G. ;
Abd-Elazem, Ibrahim S. ;
Huang, Ru Chih C. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (25) :4684-4688
[10]   Salvianolic Acid A, a Novel Matrix Metalloproteinase-9 Inhibitor, Prevents Cardiac Remodeling in Spontaneously Hypertensive Rats [J].
Jiang, Baohong ;
Li, Defang ;
Deng, Yanping ;
Teng, Fukang ;
Chen, Jing ;
Xue, Song ;
Kong, Xiangqian ;
Luo, Cheng ;
Shen, Xu ;
Jiang, Hualiang ;
Xu, Feng ;
Yang, Wengang ;
Yin, Jun ;
Wang, Yanhui ;
Chen, Hui ;
Wu, Wanying ;
Liu, Xuan ;
Guo, De-an .
PLOS ONE, 2013, 8 (03)