Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate
Qin, Xu-Jie1; Rauwolf, Tyler J.2; Li, Pan-Pan3; Liu, Hui1; McNeely, James2; Hua, Yan3; Liu, Hai-Yang1; Porco, John A., Jr.2
Corresponding AuthorLiu, Hai-Yang(haiyangliu@mail.kib.ac.cn) ; Porco, John A., Jr.(porco@bu.edu)
2019-03-22
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN1433-7851
Volume58Issue:13Pages:4291-4296
AbstractRhodomyrtusialsA-C, the first examples of triketone-sesquiterpene meroterpenoids featuring a unique 6/5/5/9/4 fused pentacyclic ring system were isolated from Rhodomyrtus tomentosa, along with several biogenetically-related dihydropyran isomers. Two bis-furans and one dihydropyran isomer showed acetylcholinesterase (AChE) inhibitory activity. Structures of the isolates were unambiguously established by a combination of spectroscopic data, ECD analysis, and total synthesis. Bioinspired total syntheses of six isolates were achieved in six steps utilizing a reactive enetrione intermediate generated in situ from a readily available hydroxy-endoperoxide precursor.
Keywordbiomimetic synthesis Diels-Alder enetrione terpenoids total synthesis
DOI10.1002/anie.201814421
Indexed BySCI
Language英语
WOS IDWOS:000462655400032
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Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/67656
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorLiu, Hai-Yang; Porco, John A., Jr.
Affiliation1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
2.Boston Univ, Ctr Mol Discovery BUCMD, Dept Chem, 590 Commonwealth Ave, Boston, MA 02215 USA
3.Southwest Forestry Univ, Coll Forestry, Kunming 650224, Yunnan, Peoples R China
Recommended Citation
GB/T 7714
Qin, Xu-Jie,Rauwolf, Tyler J.,Li, Pan-Pan,et al. Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2019,58(13):4291-4296.
APA Qin, Xu-Jie.,Rauwolf, Tyler J..,Li, Pan-Pan.,Liu, Hui.,McNeely, James.,...&Porco, John A., Jr..(2019).Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,58(13),4291-4296.
MLA Qin, Xu-Jie,et al."Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 58.13(2019):4291-4296.
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