Baylis–Hillman Acetates in Synthesis: Copper(I)/tert-Butyl Hydroperoxide Promoted One-Pot Oxidative Intramolecular Cyclization Protocol for the Preparation of Pyrrole-Fused Compounds and the Formal Synthesis of (±)-Crispine A

Abstract

A convenient one-pot protocol for the synthesis of benzo-fused and indole-fused indolizines from Baylis–Hillman acetates was developed. This strategy involves CuBr/tert-butyl hydroperoxide promoted oxidation, intramolecular cyclization, and aromatization as key steps. The efficacy of this methodology was demonstrated by the formal synthesis of (±)-crispine A, a biologically active molecule.

A one-pot, four-step strategy involving alkylation, oxidation, intramolecular cyclization, and aromatization is developed for the synthesis of pyrrole-fused tri- and tetracyclic compounds by using Baylis–Hillman acetates as the starting materials. A formal synthesis of biologically active (±)-crispine A is also achieved. EWG = electron-withdrawing group.

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