Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine

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 w...

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Detalles Bibliográficos
Autores principales: Newton, Annabella F, Rejzek, Martin, Alcaraz, Marie-Lyne, Stockman, Robert A
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2008
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2238745/
https://www.ncbi.nlm.nih.gov/pubmed/18201377
http://dx.doi.org/10.1186/1860-5397-4-4
Descripción
Sumario: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. CONCLUSIONS: 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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