Synthesis of Hydrocarbazole Derivatives by Oxidative Dearomative Cyclization of Diarylamines Using a Hypervalent
Keisuke Hosoya1, Keita Iida1, Minami Odagi1
1Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Ko-ganei City, Tokyo 184-8588, Japan.
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.
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