A highly active and selective Al-based catalytic Oppenauer (O) oxidation is reported. Quantitative and selective oxidations of a variety of benzylic, propargylic, allylic, and aliphatic primary and secondary alcohols were achieved using nitrobenzaldehyde derivatives as the oxidant and simple aluminum compounds as precatalysts.

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Alstonine and serpentine are pentacyclic indoloquinolizidine alkaloids (referred to as "anhydronium bases") containing three contiguous stereocenters.E ach possesses interesting biological activity,w ith alstonine being the major component of ap lant-based remedy to treat psychosis and other nervous system disorders.T his work describes the enantioselective total syntheses of these natural products with ac ooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step.

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Products gained from this approach can be transformed into biologically active flavonoids [e.g. (III)].