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Updated: Jan 2, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
Total Syntheses of (-)-Deoxoapodine, (-)-Kopsifoline D, and (-)-Beninine
Yi-Guo Zhou1, Henry N C Wong1,2,3, Xiao-Shui Peng1,2,3
1Department of Chemistry and State Key Laboratory of Synthetic Chemistry , The Chinese University of Hong Kong , Shatin 100051 , New Territories , Hong Kong SAR, China.
Abstract:
The total syntheses of Aspidosperma and Kopsia alkaloids (-)-deoxoapodine, (-)-kopsifoline D, and (-)-beninine are described through a domino deprotection-Michael addition-nucleophilic substitution protocol to assemble the core framework in efficient steps. Corey-Bakshi-Shibata reduction was employed to afford the enantioenriched intermediate for the total syntheses of the aforementioned alkaloids. The chirality was shown to completely transfer to the backbone using Johnson-Claisen rearrangement. The enantioselective total syntheses of (-)-kopsifoline D and (-)-beninine were accomplished for the first time. Our strategy opens up practical avenues for the total synthesis of structurally similar alkaloids.
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