Enantioselective Synthesis of (-)-N-Boc-7-azabicyclo[2.2.1]heptan-2-one and (+)-N-Boc-4-amino-2-cyclohexen-1-one: Formal Total Synthesis of Both Enantiomers of Epibatidine

Abstract

we succeeded in the stereoselective synthesis of (-)-N-Boc-7-azabicyclo[2.2.1]heptan-2-one ((-)-2) and (+)-N-Boc-4-amino-2-cyclo-hexen-1-one ((+)-3), key intermediates to (-) and (+)-epibatidine from a common chiral building block ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclohexanecarboxylate (4) This constitutes the formal total synthesis of both enantiomers of epibatidine, a potent analgesic.