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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.


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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.


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Publication History

Article published online:
22 April 2025

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