A cascade approach towards the gephyrotoxins
<p>The aim of this project was to develop a cascade approach towards perhydropyrrolo-[1,2-<em>a</em>]-quinolines and to apply this to the asymmetric synthesis of the gephyrotoxin alkoids.</p><p>Chapters Two and Three outline the development of a synthetic route towards...
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| Muut tekijät: | |
| Aineistotyyppi: | Opinnäyte |
| Kieli: | English |
| Julkaistu: |
2012
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| Aiheet: |
| _version_ | 1826315862644097024 |
|---|---|
| author | Wallace, S |
| author2 | Smith, M |
| author_facet | Smith, M Wallace, S |
| author_sort | Wallace, S |
| collection | OXFORD |
| description | <p>The aim of this project was to develop a cascade approach towards perhydropyrrolo-[1,2-<em>a</em>]-quinolines and to apply this to the asymmetric synthesis of the gephyrotoxin alkoids.</p><p>Chapters Two and Three outline the development of a synthetic route towards a range of cascade precursors, whilst Chapter Four outlines investigations into the enamine-Michael cascade. Central to understanding the cascade process was the discovery that the major product of the enamine-Michael cascade was the unusual tricyclic hydroquinium salt. This can subsequently be engaged in a diastereoselective inter- or intramolecular reduction to afford either a <em>trans-</em>perhydro-[1,2-<em>a</em>]-quinoline or a tetracyclic aminal in high overall yield depending on the C1 oxygen substituent.</p> |
| first_indexed | 2024-03-06T19:37:20Z |
| format | Thesis |
| id | oxford-uuid:1f7b55ec-0346-498c-be03-81f3b9fde2f5 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-12-09T03:33:56Z |
| publishDate | 2012 |
| record_format | dspace |
| spelling | oxford-uuid:1f7b55ec-0346-498c-be03-81f3b9fde2f52024-12-01T17:29:33ZA cascade approach towards the gephyrotoxinsThesishttp://purl.org/coar/resource_type/c_db06uuid:1f7b55ec-0346-498c-be03-81f3b9fde2f5Natural productsOrganic chemistryEnglishOxford University Research Archive - Valet2012Wallace, SSmith, M<p>The aim of this project was to develop a cascade approach towards perhydropyrrolo-[1,2-<em>a</em>]-quinolines and to apply this to the asymmetric synthesis of the gephyrotoxin alkoids.</p><p>Chapters Two and Three outline the development of a synthetic route towards a range of cascade precursors, whilst Chapter Four outlines investigations into the enamine-Michael cascade. Central to understanding the cascade process was the discovery that the major product of the enamine-Michael cascade was the unusual tricyclic hydroquinium salt. This can subsequently be engaged in a diastereoselective inter- or intramolecular reduction to afford either a <em>trans-</em>perhydro-[1,2-<em>a</em>]-quinoline or a tetracyclic aminal in high overall yield depending on the C1 oxygen substituent.</p> |
| spellingShingle | Natural products Organic chemistry Wallace, S A cascade approach towards the gephyrotoxins |
| title | A cascade approach towards the gephyrotoxins |
| title_full | A cascade approach towards the gephyrotoxins |
| title_fullStr | A cascade approach towards the gephyrotoxins |
| title_full_unstemmed | A cascade approach towards the gephyrotoxins |
| title_short | A cascade approach towards the gephyrotoxins |
| title_sort | cascade approach towards the gephyrotoxins |
| topic | Natural products Organic chemistry |
| work_keys_str_mv | AT wallaces acascadeapproachtowardsthegephyrotoxins AT wallaces cascadeapproachtowardsthegephyrotoxins |