188845-76-3Relevant articles and documents
A formal asymmetric synthesis of (-)-epibatidine using a highly diastereoselective hetero Diels-Alder reaction
Cabanal-Duvillard, Isabelle,Berrien, Jean-Fran?ois,Ghosez, Léon,Husson, Henri-Philippe,Royer, Jacques
, p. 3763 - 3769 (2007/10/03)
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 dienophite derived from (+)- camphorsultam. The resulting cycloadduct was readily transformed into the N- protected-7-azabicycto[2.2.1]heptan-2-one derivative which has previously been transformed into(-)-epibatidine. (C) 2000 Elsevier Science.