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. Holmes^1,2
• 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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