Total Synthesis of Zephycarinatines via Photocatalytic Reductive Radical ipso-Cyclization.
alkaloids
natural products
photocatalysis
radical ipso-cyclization
total synthesis
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
16 11 2020
16 11 2020
Historique:
received:
08
07
2020
pubmed:
10
8
2020
medline:
10
8
2020
entrez:
10
8
2020
Statut:
ppublish
Résumé
We report herein a nonbiomimetic strategy for the total synthesis of the plicamine-type alkaloids zephycarinatines C and D. The key feature of the synthesis is a stereoselective reductive radical ipso-cyclization using visible-light-mediated photoredox catalysis. This cyclization enabled the construction of a 6,6-spirocyclic core structure through the addition of a carbon-centered radical onto the aromatic ring. Biological evaluation of zephycarinatines and their derivatives revealed that the synthetic derivative with a keto group displays moderate inhibitory activity against LPS-induced NO production. This approach could offer future opportunities to expand the chemical diversity of plicamine-type alkaloids as well as providing useful intermediates for their syntheses.
Identifiants
pubmed: 32770565
doi: 10.1002/anie.202009399
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
21210-21215Informations de copyright
© 2020 Wiley-VCH GmbH.
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