Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2025; 21(05): 443
DOI: 10.1055/a-2558-0447
DOI: 10.1055/a-2558-0447
Synthesis of Natural Products
Total Synthesis of (–)-Rubriflordilactone B
Xie X,
Bao J,
Wang Y,
Shen Y,
Liang Z,
Tian H,
Gui J *.
Shanghai Institute of Organic Chemistry, P. R. China
Enantioselective Total Synthesis of (–)-Rubriflordilactone B by a Bioinspired Skeletal Reorganization Approach.
J. Am. Chem. Soc. 2025;
147: 7875-7885
DOI: 10.1021/jacs.4c18292
Enantioselective Total Synthesis of (–)-Rubriflordilactone B by a Bioinspired Skeletal Reorganization Approach.
J. Am. Chem. Soc. 2025;
147: 7875-7885
DOI: 10.1021/jacs.4c18292
Keywords
(–)-rubriflordilactone B - Schisandra bisnortriterpenoid - [2,3]-Wittig–Still rearrangement - Suzuki–Miyaura coupling - Friedel–Crafts cyclization - Kornblum–DeLaMare rearrangement
Significance
Gui and co-workers report the synthesis of (–)-rubriflordilactone B. The natural product was isolated in 2006 by Sun and co-workers and features an intriguing 5 /5 /7 /6 /5 /5-hexacyclic framework. Biological studies indicate potential anti-HIV activity, making it an appealing target for further studies.
#
Comment
Fragment coupling via Suzuki–Miyaura coupling followed by Friedel–Crafts cyclization affords intermediate F. Baeyer–Villiger oxidation enables an elimination–transesterification–conjugate addition cascade that forms the western 5 /5-fused ring system of (–)-rubriflordilactone B.
#
#
Publication History
Article published online:
22 April 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany