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Updated: Jul 8, 2026
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (+/-)-hippodamine
Annabella F Newton1, Martin Rejzek, Marie-Lyne Alcaraz
1School of Chemistry, University of Nottingham, Nottingham NG7 2RD, UK. pcxan4@nottingham.ac.uk
Background:
Hippodamine is a volatile defence alkaloid isolated from ladybird beetles which holds potential as an agrochemical agent and was the subject of a synthesis by our group in 2005.
Results:
Two enhancements to our previous syntheses of (+/-)-hippodamine and (+/-)-epi-hippodamine are presented which are able to shorten the syntheses by up to two steps.
Conclusion:
Key advances include a two-directional homologation by cross metathesis and a new tandem reductive amination/double intramolecular Michael addition which generates 6 new bonds, 2 stereogenic centres and two rings, giving a single diastereomer in 74% yield.
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