Synthesis of (-)-xialenon A by enantioselective alpha-deprotonation-rearrangement of a meso-epoxide
The first total synthesis of (-)-xialenon A was achieved via enantioselective transannular desymmetrisation of a substituted cycloctene oxide using an organolithium/(-)-α-isosparteine combination. Oxidation of the resulting bicyclo[3.3.0]octanol gave an enone which underwent stereoselective conjugat...
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| Format: | Journal article |
| Language: | English |
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2003
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| _version_ | 1826267108311302144 |
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| author | Hodgson, D Galano, J Christlieb, M |
| author_facet | Hodgson, D Galano, J Christlieb, M |
| author_sort | Hodgson, D |
| collection | OXFORD |
| description | The first total synthesis of (-)-xialenon A was achieved via enantioselective transannular desymmetrisation of a substituted cycloctene oxide using an organolithium/(-)-α-isosparteine combination. Oxidation of the resulting bicyclo[3.3.0]octanol gave an enone which underwent stereoselective conjugate allylation; subsequent α′-hydroxylation on the more hindered face of a derived enone using hypervalent iodine chemistry led to the natural product. © 2003 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-06T20:49:09Z |
| format | Journal article |
| id | oxford-uuid:36f926a5-45e9-42b8-99d1-c984df23c858 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T20:49:09Z |
| publishDate | 2003 |
| record_format | dspace |
| spelling | oxford-uuid:36f926a5-45e9-42b8-99d1-c984df23c8582022-03-26T13:41:11ZSynthesis of (-)-xialenon A by enantioselective alpha-deprotonation-rearrangement of a meso-epoxideJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:36f926a5-45e9-42b8-99d1-c984df23c858EnglishSymplectic Elements at Oxford2003Hodgson, DGalano, JChristlieb, MThe first total synthesis of (-)-xialenon A was achieved via enantioselective transannular desymmetrisation of a substituted cycloctene oxide using an organolithium/(-)-α-isosparteine combination. Oxidation of the resulting bicyclo[3.3.0]octanol gave an enone which underwent stereoselective conjugate allylation; subsequent α′-hydroxylation on the more hindered face of a derived enone using hypervalent iodine chemistry led to the natural product. © 2003 Elsevier Ltd. All rights reserved. |
| spellingShingle | Hodgson, D Galano, J Christlieb, M Synthesis of (-)-xialenon A by enantioselective alpha-deprotonation-rearrangement of a meso-epoxide |
| title | Synthesis of (-)-xialenon A by enantioselective alpha-deprotonation-rearrangement of a meso-epoxide |
| title_full | Synthesis of (-)-xialenon A by enantioselective alpha-deprotonation-rearrangement of a meso-epoxide |
| title_fullStr | Synthesis of (-)-xialenon A by enantioselective alpha-deprotonation-rearrangement of a meso-epoxide |
| title_full_unstemmed | Synthesis of (-)-xialenon A by enantioselective alpha-deprotonation-rearrangement of a meso-epoxide |
| title_short | Synthesis of (-)-xialenon A by enantioselective alpha-deprotonation-rearrangement of a meso-epoxide |
| title_sort | synthesis of xialenon a by enantioselective alpha deprotonation rearrangement of a meso epoxide |
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