Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www-thieme-connect-de.accesdistant.sorbonne-universite.fr/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2025; 21(07): 661
DOI: 10.1055/a-2601-4040
DOI: 10.1055/a-2601-4040
Synthesis of Natural Products
Total Synthesis of (–)-Bisdehydrostemoninine
Akkawi NR,
Nicewicz DA *.
University of North Carolina at Chapel Hill, USA
Photochemically Enabled Total Syntheses of Stemoamide Alkaloids.
J. Am. Chem. Soc. 2025;
147: 15482-15489
DOI: 10.1021/jacs.5c01788
Photochemically Enabled Total Syntheses of Stemoamide Alkaloids.
J. Am. Chem. Soc. 2025;
147: 15482-15489
DOI: 10.1021/jacs.5c01788
Keywords
(–)-bisdehydrostemoninine - stemoamide alkaloids - hydroarylation - photoredox carbolactonization - Petasis olefination - Mitsunobu reaction - skeletal rearrangement - photoredox HAT - reductive lactonization
Significance
Akkawi and Nicewicz report the total synthesis of (–)-bisdehydrostemoninine, a stemona alkaloid bearing a 5 /7 /5 tricyclic core. The molecule further features an unusual oxaspirocyclic butenolide. The synthetic approach presented by the authors employs various photochemical transformations.
#
Comment
The synthesis hinges on a key skeletal rearrangement from pyridinium salt K to pyrrole M. A further salient step in the synthesis involves a photochemical reductive cyclization to afford (–)-bisdehydrostemoninine from another natural product of the same class.
#
#
Publication History
Article published online:
23 June 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany