Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement.
Starting from readily available (S)-styrene oxide an asymmetric synthesis is described of the naturally occurring anti-HIV spirolactone (-)-hyperolactone C, which possesses adjacent fully substituted stereocenters. The key step involves a stereocontrolled Rh(II) -catalysed oxonium ylide formation-[2...
| Main Authors: | , |
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| Format: | Journal article |
| Language: | English |
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2011
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| _version_ | 1797072593194319872 |
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| author | Hodgson, D Man, S |
| author_facet | Hodgson, D Man, S |
| author_sort | Hodgson, D |
| collection | OXFORD |
| description | Starting from readily available (S)-styrene oxide an asymmetric synthesis is described of the naturally occurring anti-HIV spirolactone (-)-hyperolactone C, which possesses adjacent fully substituted stereocenters. The key step involves a stereocontrolled Rh(II) -catalysed oxonium ylide formation-[2,3] sigmatropic rearrangement of an α-diazo-β-ketoester bearing allylic ether functionality. From the resulting furanone, an acid-catalysed lactonisation and dehydrogenation gives the natural product. |
| first_indexed | 2024-03-06T23:09:58Z |
| format | Journal article |
| id | oxford-uuid:651e0cbb-2f02-4dce-8a70-c1c662723b9b |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T23:09:58Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | oxford-uuid:651e0cbb-2f02-4dce-8a70-c1c662723b9b2022-03-26T18:23:27ZSynthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:651e0cbb-2f02-4dce-8a70-c1c662723b9bEnglishSymplectic Elements at Oxford2011Hodgson, DMan, SStarting from readily available (S)-styrene oxide an asymmetric synthesis is described of the naturally occurring anti-HIV spirolactone (-)-hyperolactone C, which possesses adjacent fully substituted stereocenters. The key step involves a stereocontrolled Rh(II) -catalysed oxonium ylide formation-[2,3] sigmatropic rearrangement of an α-diazo-β-ketoester bearing allylic ether functionality. From the resulting furanone, an acid-catalysed lactonisation and dehydrogenation gives the natural product. |
| spellingShingle | Hodgson, D Man, S Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement. |
| title | Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement. |
| title_full | Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement. |
| title_fullStr | Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement. |
| title_full_unstemmed | Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement. |
| title_short | Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement. |
| title_sort | synthesis of the anti hiv agent hyperolactone c by using oxonium ylide formation rearrangement |
| work_keys_str_mv | AT hodgsond synthesisoftheantihivagenthyperolactonecbyusingoxoniumylideformationrearrangement AT mans synthesisoftheantihivagenthyperolactonecbyusingoxoniumylideformationrearrangement |