Isolation and synthesis of novel meroterpenoids from rhodomyrtus tomentosa: investigation of a reactive enetrione intermediate
Rauwolf, Tyler J.
Porco, John A.
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Citation (published version)Xu-Jie Qin, Tyler J Rauwolf, Pan-Pan Li, Hui Liu, James McNeely, Yan Hua, Hai-Yang Liu, John A Porco. 2019. "Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate.." Angew Chem Int Ed Engl, Volume 58, Issue 13, pp. 4291 - 4296. https://doi.org/10.1002/anie.201814421
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.