Isolation and Synthesis of Novel Meroterpenoids from  Rhodomyrtus tomentos a: Investigation of a Reactive Enetrione Intermediate | Zendy

Qin XuJie | Zendy; Rauwolf Tyler J. | Zendy; Li PanPan | Zendy; Liu Hui | Zendy; McNeely James | Zendy; Hua Yan | Zendy; Liu HaiYang | Zendy; Porco John A. | Zendy

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Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentos a: Investigation of a Reactive Enetrione Intermediate

Author(s) -

Qin XuJie,

Rauwolf Tyler J.,

Li PanPan,

Liu Hui,

McNeely James,

Hua Yan,

Liu HaiYang,

Porco John A.

Publication year - 2019

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201814421

Subject(s) - dihydropyran , stereochemistry , chemistry , sesquiterpene , total synthesis , terpene , ring (chemistry) , acetylcholinesterase , aché , organic chemistry , enzyme , catalysis

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.

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