Organosilicon reagents in carbon-carbon bond forming reactions: towards the total synthesis of incednine
<p>This thesis investigates a total synthesis of the incednine aglycon by utilising alkenylsilane reagents to assemble the pentaenyl and tetraenyl systems through cross-coupling reactions. The early chapters develop methodology to access both cyclic alkenylsiloxanes and functionalised (E)-alke...
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| Format: | Thesis |
| Language: | English |
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2013
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| _version_ | 1797092259435380736 |
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| author | Lim, D |
| author2 | Anderson, E |
| author_facet | Anderson, E Lim, D |
| author_sort | Lim, D |
| collection | OXFORD |
| description | <p>This thesis investigates a total synthesis of the incednine aglycon by utilising alkenylsilane reagents to assemble the pentaenyl and tetraenyl systems through cross-coupling reactions. The early chapters develop methodology to access both cyclic alkenylsiloxanes and functionalised (E)-alkenylsilanes by the controlled hydrogenation of alkynylsiloxanes and silylolefination of aldehydes, respectively, and culminate in the synthesis of a C6-C13 <em>bis</em>(alkenylsilane)incednine fragment (Scheme 1).</p> <p>The C1-C5 and C14-C23 coupling partners are synthesised in three and ten steps from propargyl alcohol and L-alanine methyl ester through phosphorous-based olefination strategies. In the final chapter we describe our first generation approach to incednine which entails orthogonal cross-couplings to construct the C5-C6 and C13-C14 bonds (Scheme 2).</p> |
| first_indexed | 2024-03-07T03:43:35Z |
| format | Thesis |
| id | oxford-uuid:beb3e9cb-087d-4c96-97f4-da611d08f9f9 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T03:43:35Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | oxford-uuid:beb3e9cb-087d-4c96-97f4-da611d08f9f92022-03-27T05:41:47ZOrganosilicon reagents in carbon-carbon bond forming reactions: towards the total synthesis of incednineThesishttp://purl.org/coar/resource_type/c_db06uuid:beb3e9cb-087d-4c96-97f4-da611d08f9f9Natural productsOrganic chemistryOrganic synthesisEnglishOxford University Research Archive - Valet2013Lim, DAnderson, E<p>This thesis investigates a total synthesis of the incednine aglycon by utilising alkenylsilane reagents to assemble the pentaenyl and tetraenyl systems through cross-coupling reactions. The early chapters develop methodology to access both cyclic alkenylsiloxanes and functionalised (E)-alkenylsilanes by the controlled hydrogenation of alkynylsiloxanes and silylolefination of aldehydes, respectively, and culminate in the synthesis of a C6-C13 <em>bis</em>(alkenylsilane)incednine fragment (Scheme 1).</p> <p>The C1-C5 and C14-C23 coupling partners are synthesised in three and ten steps from propargyl alcohol and L-alanine methyl ester through phosphorous-based olefination strategies. In the final chapter we describe our first generation approach to incednine which entails orthogonal cross-couplings to construct the C5-C6 and C13-C14 bonds (Scheme 2).</p> |
| spellingShingle | Natural products Organic chemistry Organic synthesis Lim, D Organosilicon reagents in carbon-carbon bond forming reactions: towards the total synthesis of incednine |
| title | Organosilicon reagents in carbon-carbon bond forming reactions: towards the total synthesis of incednine |
| title_full | Organosilicon reagents in carbon-carbon bond forming reactions: towards the total synthesis of incednine |
| title_fullStr | Organosilicon reagents in carbon-carbon bond forming reactions: towards the total synthesis of incednine |
| title_full_unstemmed | Organosilicon reagents in carbon-carbon bond forming reactions: towards the total synthesis of incednine |
| title_short | Organosilicon reagents in carbon-carbon bond forming reactions: towards the total synthesis of incednine |
| title_sort | organosilicon reagents in carbon carbon bond forming reactions towards the total synthesis of incednine |
| topic | Natural products Organic chemistry Organic synthesis |
| work_keys_str_mv | AT limd organosiliconreagentsincarboncarbonbondformingreactionstowardsthetotalsynthesisofincednine |