Perhydropyrrolo[1,2-α]indole synthesis: Diastereoselection in an intramolecular conjugate addition of an amine to a 1,4-cyclohexadienone

Article abstract of DOI:10.1016/S0040-4020(97)90397-5

Cyclization of amino-cyclohexadienone 4 occurs with a high level of diastereoselection to afford perhydroindole 13. The relationship of this observation to controlling the relative stereochemistry between C₃₄ and other stereogenic centers in the manzamine family of alkaloids is discussed.