Regioselective reduction of N-alkyl-3-sulfonyl-glutarimide. Formal synthesis of 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a] quinolizine and homobaclofen

摘要

Reduction of N-alkyl-3-sulfonylglutarimides with (1) sodium hydride and then with lithium aluminum hydride, or (2) sodium borohydride yielded two different y6pes of regioselectively reduced hydroxypiperidinones with were further dehydrated to two pyridin-2-ones in the presence of boron trifluoride etherate. Cycloaddition and regioselective reduction were combined to synthesize 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a] quinolizine and homobaclofen.