Flow synthesis of tricyclic spiropiperidines as building blocks for the histrionicotoxin family of alkaloids

    • Malte Brasholz1
    • Brian A. Johnson2
    • James M. Macdonald1
    • Anastasios Polyzos1
    • John Tsanaktsidis1
    • Simon Saubern1
    • Andrew B. Holmes1,2
    • John H. Ryan1
    • 1CSIRO Molecular and Health Technologies, Victoria, Australia
    • 2School of Chemistry, Bio 21 Institute, University of Melbourne, Victoria, Australia

    A domino cyclization reaction of the bis-unsaturated ketone 3 with hydroxylamine proceeds with good yield and high stereoselectivity, in a flow reactor system. The tricyclic spiropiperidine products 5 and 2 obtained are valuable building blocks for the synthesis of analogues of the histrionicotoxin alkaloids.

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