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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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
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author Newton, Annabella F
Rejzek, Martin
Alcaraz, Marie-Lyne
Stockman, Robert A
author_facet Newton, Annabella F
Rejzek, Martin
Alcaraz, Marie-Lyne
Stockman, Robert A
author_sort Newton, Annabella F
collection PubMed
description 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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spelling pubmed-22387452008-02-12 Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine Newton, Annabella F Rejzek, Martin Alcaraz, Marie-Lyne Stockman, Robert A Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2008-01-17 /pmc/articles/PMC2238745/ /pubmed/18201377 http://dx.doi.org/10.1186/1860-5397-4-4 Text en Copyright © 2008, Newton et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Newton, Annabella F
Rejzek, Martin
Alcaraz, Marie-Lyne
Stockman, Robert A
Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine
title Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine
title_full Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine
title_fullStr Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine
title_full_unstemmed Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine
title_short Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine
title_sort combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine
topic Full Research Paper
url 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
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