Tetrahedron

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

…, JM Macdonald, A Polyzos, J Tsanaktsidis, S Saubern…

Index: Brasholz, Malte; Johnson, Brian A.; Macdonald, James M.; Polyzos, Anastasios; Tsanaktsidis, John; Saubern, Simon; Holmes, Andrew B.; Ryan, John H. Tetrahedron, 2010 , vol. 66, # 33 p. 6445 - 6449

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Citation Number: 32

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.