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Synfacts 2025; 21(05): 443
DOI: 10.1055/a-2558-0447
Synthesis of Natural Products

Total Synthesis of (–)-Rubriflordilactone B

Contributor(s):
Erick M. Carreira 
,
Alexander Hamminger
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
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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

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