Total Synthesis of Zephycarinatines via Photocatalytic Reductive Radical ipso-Cyclization.
Angew Chem Int Ed Engl
; 59(47): 21210-21215, 2020 11 16.
Article
em En
| MEDLINE
| ID: mdl-32770565
ABSTRACT
We report herein a nonbiomimetic strategy for the total synthesis of the plicamine-type alkaloids zephycarinatinesâ
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.
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Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article
País de afiliação:
Japão