Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate
Abstract
Rhodomyrtusials A–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.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Feb 20, 2019
- Source ID
- 10.1002/ange.201814421
Entities
People
- Hai‐yang Liu
- Hui Liu
- James Mcneely
- John A. Porco
- Pan‐pan Li
- Tyler J. Rauwolf
- Xu‐jie Qin
- Yan Hua
Organizations
- Boston University
- Defense Advanced Research Projects Agency
- Kunming Institute of Botany
- National Institutes of Health
- National Natural Science Foundation of China
- Southwest Forestry University
- Youth Innovation Promotion Association