Synthesis of the ABCDG ring skeleton of communesin F based on carboborylation of 1,3-diene and Bi(OTf)
Journal
The Journal of antibiotics
ISSN: 1881-1469
Titre abrégé: J Antibiot (Tokyo)
Pays: England
ID NLM: 0151115
Informations de publication
Date de publication:
06 2019
06 2019
Historique:
received:
16
11
2018
accepted:
26
12
2018
revised:
18
12
2018
pubmed:
15
2
2019
medline:
5
11
2019
entrez:
15
2
2019
Statut:
ppublish
Résumé
Communesins, isolated from the mycelium of a strain of Penicillium sp., are cytotoxic heptacyclic indole alkaloids bearing a bis-aminal structure and two contiguous quaternary carbon centers. Toward a total synthesis of communesin F, we synthesized a pentacyclic ABCDG ring skeleton via carboborylation of 1,3-diene and a Friedel-Crafts-type cyclization, resulting in the formation of an azepine ring through a Bi(OTf)
Identifiants
pubmed: 30760839
doi: 10.1038/s41429-019-0142-7
pii: 10.1038/s41429-019-0142-7
doi:
Substances chimiques
Heterocyclic Compounds, 4 or More Rings
0
communesin F
0
Palladium
5TWQ1V240M
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM