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
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.
