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

Abstract

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. © 2010 Elsevier Ltd.