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

The Journal of Organic Chemistry
2020.0

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. Copyright © 2020 American Chemical Society.

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