Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine
Background<p>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.</p><p>Results</p><p>Two enhancements to our previous syntheses of (±)-hippodami...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2008-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Online Access: | https://doi.org/10.1186/1860-5397-4-4 |
| _version_ | 1818657392490971136 |
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| author | Annabella F. Newton Martin Rejzek Marie-Lyne Alcaraz Robert A. Stockman |
| author_facet | Annabella F. Newton Martin Rejzek Marie-Lyne Alcaraz Robert A. Stockman |
| author_sort | Annabella F. Newton |
| collection | DOAJ |
| description | Background<p>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.</p><p>Results</p><p>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.</p><p>Conclusions</p><p>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.</p> |
| first_indexed | 2024-12-17T03:40:45Z |
| format | Article |
| id | doaj.art-0b1308118b8b4411a23e46d3af657bba |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T03:40:45Z |
| publishDate | 2008-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-0b1308118b8b4411a23e46d3af657bba2022-12-21T22:05:00ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972008-01-0141410.1186/1860-5397-4-41860-5397-4-4Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamineAnnabella F. Newton0Martin Rejzek1Marie-Lyne Alcaraz2Robert A. Stockman3School of Chemistry, University of Nottingham, Nottingham NG7 2RD, UKSchool of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, UKAstraZeneca, Bakewell Road, Loughborough, Leics LE11 5RH, UKSchool of Chemistry, University of Nottingham, Nottingham NG7 2RD, UKBackground<p>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.</p><p>Results</p><p>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.</p><p>Conclusions</p><p>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.</p>https://doi.org/10.1186/1860-5397-4-4 |
| spellingShingle | Annabella F. Newton Martin Rejzek Marie-Lyne Alcaraz Robert A. Stockman Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine Beilstein Journal of Organic Chemistry |
| 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 |
| url | https://doi.org/10.1186/1860-5397-4-4 |
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