4.5 Article

Combining two-directional synthesis and tandem reactions, part II:: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine

Journal

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 4, Issue -, Pages -

Publisher

BEILSTEIN-INSTITUT
DOI: 10.1186/1860-5397-4-4

Keywords

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Funding

  1. EPSRC [EP/E055346/2] Funding Source: UKRI
  2. Engineering and Physical Sciences Research Council [EP/E055346/2] Funding Source: researchfish

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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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