Total Synthesis of Isohericenone J via a Stille Coupling Reaction.

Catalysis Indole Alkaloids / chemical synthesis Molecular Structure

Journal

Journal of natural products
ISSN: 1520-6025
Titre abrégé: J Nat Prod
Pays: United States
ID NLM: 7906882

Informations de publication

Date de publication:
22 05 2020
Historique:
pubmed: 1 5 2020
medline: 30 7 2021
entrez: 1 5 2020
Statut: ppublish

Résumé

The first total synthesis of isohericenone J is reported. Key features of this synthetic strategy are a Friedel-Crafts reaction to construct the isobenzofuranone unit and a Pd-catalyzed Stille coupling reaction for the formation of the C5-C1' bond, generating the natural product, as well as one of its isomers, in 6.0% overall yield in eight steps. This strategy provides a foundation for the synthesis of challenging isobenzofuranone and isoindolinone-type derivatives.

Identifiants

DOI: 10.1021/acs.jnatprod.9b01251 PMID: 32352292
pubmed: 32352292
doi: 10.1021/acs.jnatprod.9b01251
doi:

Substances chimiques

Indole Alkaloids 0
isohericenone 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

1701-1705

Auteurs

Wei Cao (W)

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Yushan Road, Qingdao, 266003, People's Republic of China.

Ping Chen (P)

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Yushan Road, Qingdao, 266003, People's Republic of China.

Yu Tang (Y)

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Yushan Road, Qingdao, 266003, People's Republic of China.
Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, 266237, People's Republic of China.
ORCID: 0000-0001-8224-4639

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Classifications MeSH

questionsmedicales.fr › Phénomènes chimiques › Catalyse › Total Synthesis of Isohericenone J via a...
questionsmedicales.fr › Composés hétérocycliques › Composés hétérocycliques à cycles fusionnés › Composés hétérobicycliques › Indolizine › Indolizidines › Alcaloïdes indoliques › Total Synthesis of Isohericenone J via a...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Total Synthesis of Isohericenone J via a...