Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate.
Angew Chem Int Ed Engl
; 58(13): 4291-4296, 2019 03 22.
Article
em En
| MEDLINE
| ID: mdl-30681258
ABSTRACT
Rhodomyrtusialsâ
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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Texto completo:
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Base de dados:
MEDLINE
Assunto principal:
Acetilcolinesterase
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Sesquiterpenos
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Terpenos
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Extratos Vegetais
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Myrtaceae
Limite:
Humans
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2019
Tipo de documento:
Article