Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5272173 | Tetrahedron Letters | 2009 | 4 Pages |
Abstract
The asymmetric BF3·Et2O catalyzed nucleophilic reactions of 3-silyloxypiperidine N,O-acetal 10 with silyl enol ethers derived from ketones are described. (+)-Febrifugine 1, an antimalarial alkaloid, was successfully synthesized based on this nucleophilic substitution. In addition, N,O-acetal 10 was synthesized from l-benzyl glutamate in 11 steps.
Graphical abstractThe asymmetric BF3·Et2O-catalyzed nucleophilic reactions of 3-silyloxypiperidine N,O-acetal 10 with silyl enol ethers derived from ketones are described. (+)-Febrifugine 1, an antimalarial alkaloid, was successfully synthesized based on this nucleophilic substitution.Download full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Ru-Cheng Liu, Wei Huang, Jing-Yi Ma, Bang-Guo Wei, Guo-Qiang Lin,