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A novel spiropiperidine system I i.e. an aza structural analog of histrionicotoxin was constructed from 2-cyano-6-phenyloxazolopiperidine synthon II. The suitable quaternary carbon was created by alkylation at the position alpha to the nitrile followed by transformation of the nitrile group into a primary amine. Final aminoreductive cyclization gave the spiro system. [on SciFinder (R)]
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Woongbae Lee, Yun Ho Lee, Jaedon Shin
Jérôme Waser, Franck Le Vaillant, Stephanie Grace Elizabeth Amos