Catalyst-Free sp(3) C-H Acyloxylation: Regioselective Synthesis of 1-Acyloxy Derivatives of the Natural Product Tanshinone IIA

doi:10.1021/acs.jnatprod.6b00370

	Catalyst-Free sp(3) C-H Acyloxylation: Regioselective Synthesis of 1-Acyloxy Derivatives of the Natural Product Tanshinone IIA
	Ding, Chunyong 1,3; Li, Jie1,2 ; Jiao, Mingkun 1,3; Zhang, Ao1,2,3
	2016-10
发表期刊	JOURNAL OF NATURAL PRODUCTS (IF:3.3[JCR-2023],3.9[5-Year])
ISSN	0163-3864
卷号	79 期号:10 页码:2514-2520
发表状态	已发表
DOI	10.1021/acs.jnatprod.6b00370
摘要	Tanshinone IIA is a valuable bioactive natural product isolated from the well-known Chinese herb Danshen. Structural manipulation of the A-ring of tanshinone IIA is rather limited. In this study, a substrate tautomerization-induced catalyst-free benzylic sp(3) C-H acyloxylation approach is reported that allows the direct introduction of various acyloxy groups at the A-ring benzylic methylene of various tanshinone IIA substrates, thus avoiding the use of expensive transition metal catalysts and the production of harmful byproducts. This approach features a unique acid-induced reversible enolization/oxa-conjugate addition process followed by oxidation to exclusively give a series of diverse 1-acyloxylated derivatives under simple conditions in a regioselective manner. Compared with the literature procedures, this protocol demonstrates a higher efficiency, a more robust functional-group tolerance, atom economy, and lower cost.
收录类别	SCI ; IC ; CCR
语种	英语
资助项目	Pujiang Talent Project from the Shanghai Commission of Science and Technology[14PJ1410700]
WOS研究方向	Plant Sciences ; Pharmacology & Pharmacy
WOS类目	Plant Sciences ; Chemistry, Medicinal ; Pharmacology & Pharmacy
WOS记录号	WOS:000386745300012
出版者	AMER CHEMICAL SOC
WOS关键词	FREE OXIDATIVE ESTERIFICATION ; SALVIA-MILTIORRHIZA BUNGE ; VASODILATIVE ACTIVITY ; BOND ACTIVATION ; FUNCTIONALIZATION ; CYCLOALKANES ; CHEMISTRY ; ARYLATION ; ALDEHYDES ; STRATEGY
原始文献类型	Article
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/1683
专题	生命科学与技术学院生命科学与技术学院_特聘教授组_张翱组生命科学与技术学院_博士生
通讯作者	Zhang, Ao
作者单位	1.Chinese Acad Sci, Shanghai Inst Mat Med, Synthet Organ & Med Chem Lab, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China 2.ShanghaiTech Univ, Shanghai 20120, Peoples R China 3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
通讯作者单位	上海科技大学
推荐引用方式 GB/T 7714	Ding, Chunyong,Li, Jie,Jiao, Mingkun,et al. Catalyst-Free sp(3) C-H Acyloxylation: Regioselective Synthesis of 1-Acyloxy Derivatives of the Natural Product Tanshinone IIA[J]. JOURNAL OF NATURAL PRODUCTS,2016,79(10):2514-2520.
APA	Ding, Chunyong,Li, Jie,Jiao, Mingkun,&Zhang, Ao.(2016).Catalyst-Free sp(3) C-H Acyloxylation: Regioselective Synthesis of 1-Acyloxy Derivatives of the Natural Product Tanshinone IIA.JOURNAL OF NATURAL PRODUCTS,79(10),2514-2520.
MLA	Ding, Chunyong,et al."Catalyst-Free sp(3) C-H Acyloxylation: Regioselective Synthesis of 1-Acyloxy Derivatives of the Natural Product Tanshinone IIA".JOURNAL OF NATURAL PRODUCTS 79.10(2016):2514-2520.