Title of article
BF3·Et2O catalyzed diastereoselective nucleophilic reactions of 3-silyloxypiperidine N,O-acetal with silyl enol ether and application to the asymmetric synthesis of (+)-febrifugine
Author/Authors
Liu، نويسنده , , Ru-Cheng and Huang، نويسنده , , Wei and Ma، نويسنده , , Jing-Yi and Wei، نويسنده , , Bang-Guo and Lin، نويسنده , , Guo-Qiang، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2009
Pages
4
From page
4046
To page
4049
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.
Keywords
asymmetric synthesis , nucleophilic substitution , N , O-acetal , alkaloid , Piperidine
Journal title
Tetrahedron Letters
Serial Year
2009
Journal title
Tetrahedron Letters
Record number
1864862
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