Title of article
A Formal Asymmetric Synthesis of (−)-Epibatidine Using a Highly Diastereoselective Hetero Diels–Alder Reaction
Author/Authors
Isabelle Cabanal-Duvillard، نويسنده , , Jean-François Berrien، نويسنده , , Léon Ghosez، نويسنده , , Henri-Philippe Husson، نويسنده , , Jacques Royer، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2000
Pages
7
From page
3763
To page
3769
Abstract
A formal asymmetric synthesis of (−)-epibatidine is reported. The key step of the synthesis is a regio- and diastereoselective cycloaddition of silyloxycyclohexadiene with the acylnitroso dienophile derived from (+)-camphorsultam. The resulting cycloadduct was readily transformed into the N-protected-7-azabicyclo[2.2.1]heptan-2-one derivative which has previously been transformed into (−)-epibatidine.
Keywords
acylnitroso compounds , hetero Diels–Alder cycloaddition , Asymmetric synthesis , (?)-epibatidine
Journal title
Tetrahedron
Serial Year
2000
Journal title
Tetrahedron
Record number
1080865
Link To Document