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Flow synthesis of tricyclic spiropiperidines as building blocks for the histrionicotoxin family of alkaloids |
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| Authors: | Malte Brasholz Brian A. Johnson Anastasios Polyzos Simon Saubern John H. Ryan |
| Affiliation: | a CSIRO Molecular and Health Technologies, Bayview Avenue, Clayton, VIC 3168, Australia b School of Chemistry, Bio 21 Institute, University of Melbourne, Parkville, VIC 3010, Australia |
| 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. |
| Keywords: | Flow chemistry Domino reactions Spiropiperidines Olefination reactions 1,3-Dipolar cycloaddition |
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