Premium
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 , terpene , total synthesis , acetylcholinesterase , ring (chemistry) , 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.