Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 13, Pages 4291-4296Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201814421
Keywords
biomimetic synthesis; Diels-Alder; enetrione; terpenoids; total synthesis
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Funding
- National Natural Science Foundation of China [U1802287, 31600283]
- National Institutes of Health [R35 GM-118173]
- Major Bio-Medical Project of Yunnan Province [2018ZF005]
- Youth Innovation Promotion Association CAS
- Key Research and Development Plan of Yunnan Province-Special Project of Science and Technology in Yunnan Province [2017IB007]
- Innovation Team of the Ministry of Education [IRT-17R49]
- DARPA [W911NF-18-1-0025]
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RhodomyrtusialsA-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.
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