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The synthesis of the biologically active alkaloid simulenoline, isolated from the roots of Zanthoxylum simulans, is reported. The natural product was assembled from simple commercial reagents via initial domino Knoevenagel/oxa-6π-electrocyclization followed by a one-pot singlet-oxygen ene-reaction/reduction sequence. New insights of singlet oxygen reactivity with olefinic substrates have been revealed.
Martín J. Riveira (Wed,) studied this question.