Synthesis of Hydrocarbazole Derivatives by Oxidative Dearomative Cyclization of Diarylamines Using a Hypervalent Iodine Reagent.

Abstract

Hydrocarbazole derivatives bearing a quaternary stereogenic center at C4a were synthesized by means of intramolecular oxidative dearomatization of diarylamines using hypervalent iodine in moderate to good yields. The hydrocarbazole bearing a cyclohexadienone moiety was further converted into the tetracyclic skeletons of Aspidosperma and akuammiline-type alkaloids via regioselective aza-Michael reaction at C4 and at C9a, respectively.