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Total synthesis and antiviral activity of indolosesquiterpenoids from the xiamycin and oridamycin families
Alternative TitleTotal synthesis and antiviral activity of indolosesquiterpenoids from the xiamycin and oridamycin families
Meng ZC(孟占朝)1; Yu HX(于海昕)1; Li L(李莉)1; Tao WY(陶万银)1; Chen H(陈浩)1; Wan M(万明)1; Yang P(杨鹏)1; EDMONDS DAVID J1; Zhong J(钟劲)1; Li A(李昂)1
2015
Source PublicationNat. Commun.
Volume6Pages:6096
AbstractIndolosesquiterpenoids are a growing class of natural products that exhibit a wide range of biological activities. Here, we report the total syntheses of xiamycin A and oridamycins A and B, indolosesquiterpenoids isolated from Streptomyces. Two parallel strategies were exploited to forge the carbazole core: 6p-electrocyclization/aromatization and indole C2-H bond activation/Heck annulation. The construction of their trans-decalin motifs relied on two diastereochemically complementary radical cyclization reactions mediated by Ti(III) and Mn(III), respectively. The C23 hydroxyl of oridamycin B was introduced by an sp(3) C-H bond oxidation at a late stage. On the basis of the chemistry developed, the dimeric congener dixiamycin C has been synthesized for the first time. Evaluation of the antiviral activity of these compounds revealed that xiamycin A is a potent agent against herpes simplex virus-1 (HSV-1) in vitro.
Subtype论文
Subject Area生命有机化学
DOI10.1038/ncomms7096
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000350196900002
Citation statistics
Cited Times:60[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39490
Collection生命有机化学国家重点实验室
Corresponding AuthorLi A(李昂)
Affiliation1.中科院上海有机化学研究所, 生命有机化学国家重点实验室
2.中科院上海生命科学研究院
3.辉瑞全球研发中心
4.南京化学生命科学协同创新中心
Recommended Citation
GB/T 7714
Meng ZC,Yu HX,Li L,et al. Total synthesis and antiviral activity of indolosesquiterpenoids from the xiamycin and oridamycin families[J]. Nat. Commun.,2015,6:6096.
APA 孟占朝.,于海昕.,李莉.,陶万银.,陈浩.,...&李昂.(2015).Total synthesis and antiviral activity of indolosesquiterpenoids from the xiamycin and oridamycin families.Nat. Commun.,6,6096.
MLA 孟占朝,et al."Total synthesis and antiviral activity of indolosesquiterpenoids from the xiamycin and oridamycin families".Nat. Commun. 6(2015):6096.
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