Synthesis of (+)-obtusenyne
An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. The trans substituents across the...
| Main Authors: | , , , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Wiley
2008
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| _version_ | 1797106262261891072 |
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| author | Mak, S Curtis, N Payne, A Congreve, MS Wildsmith, A Francis, C Davies, J Pascu, S Burton, J Holmes, AB |
| author_facet | Mak, S Curtis, N Payne, A Congreve, MS Wildsmith, A Francis, C Davies, J Pascu, S Burton, J Holmes, AB |
| author_sort | Mak, S |
| collection | OXFORD |
| description | An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. The trans substituents across the ether linkage were established by using a transition-metalcatalyzed intramolecular hydrosilation reaction of an exo-cyclic enol ether. In addition, a formal synthesis of ent-obtusenyne from 2-deoxy-D-ribose is reported. A number of interesting points regarding the chemistry of mediumring oxygen heterocycles are highlighted. © 2008 Wiley-VCH Verlag GmbH and Co. KGaA. |
| first_indexed | 2024-03-07T06:59:13Z |
| format | Journal article |
| id | oxford-uuid:ff29907b-3326-41ec-af46-696e0862d57d |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:59:13Z |
| publishDate | 2008 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:ff29907b-3326-41ec-af46-696e0862d57d2022-03-27T13:42:35ZSynthesis of (+)-obtusenyneJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:ff29907b-3326-41ec-af46-696e0862d57dEnglishSymplectic Elements at OxfordWiley2008Mak, SCurtis, NPayne, ACongreve, MSWildsmith, AFrancis, CDavies, JPascu, SBurton, JHolmes, ABAn enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. The trans substituents across the ether linkage were established by using a transition-metalcatalyzed intramolecular hydrosilation reaction of an exo-cyclic enol ether. In addition, a formal synthesis of ent-obtusenyne from 2-deoxy-D-ribose is reported. A number of interesting points regarding the chemistry of mediumring oxygen heterocycles are highlighted. © 2008 Wiley-VCH Verlag GmbH and Co. KGaA. |
| spellingShingle | Mak, S Curtis, N Payne, A Congreve, MS Wildsmith, A Francis, C Davies, J Pascu, S Burton, J Holmes, AB Synthesis of (+)-obtusenyne |
| title | Synthesis of (+)-obtusenyne |
| title_full | Synthesis of (+)-obtusenyne |
| title_fullStr | Synthesis of (+)-obtusenyne |
| title_full_unstemmed | Synthesis of (+)-obtusenyne |
| title_short | Synthesis of (+)-obtusenyne |
| title_sort | synthesis of obtusenyne |
| work_keys_str_mv | AT maks synthesisofobtusenyne AT curtisn synthesisofobtusenyne AT paynea synthesisofobtusenyne AT congrevems synthesisofobtusenyne AT wildsmitha synthesisofobtusenyne AT francisc synthesisofobtusenyne AT daviesj synthesisofobtusenyne AT pascus synthesisofobtusenyne AT burtonj synthesisofobtusenyne AT holmesab synthesisofobtusenyne |