Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 47, Pages 21210-21215Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202009399
Keywords
alkaloids; natural products; photocatalysis; radicalipso-cyclization; total synthesis
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Funding
- JSPS KAKENHI [JP20K06938, 20H04773, 17H03971]
- AMED [JP19gm1010007]
- Grants-in-Aid for Scientific Research [17H03971, 20H04773] Funding Source: KAKEN
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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 radicalipso-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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