Enantioselective total synthesis of (+)-incargranine A enabled by bifunctional iminophosphorane and iridium catalysis
Herein we report the first enantioselective total synthesis of (+)-incargranine A, in nine steps. The total synthesis was enabled by an enantioselective intramolecular organocatalysed desymmetrising Michael addition of a malonamate ester to a linked dienone substrate that established pivotal stereoc...
| Main Authors: | , , , |
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| Format: | Journal article |
| Language: | English |
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Wiley
2023
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| _version_ | 1826312889298845696 |
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| author | Miller, AAM Biallas, P Shennan, BDA Dixon, DJ |
| author_facet | Miller, AAM Biallas, P Shennan, BDA Dixon, DJ |
| author_sort | Miller, AAM |
| collection | OXFORD |
| description | Herein we report the first enantioselective total synthesis of (+)-incargranine A, in nine steps. The total synthesis was enabled by an enantioselective intramolecular organocatalysed desymmetrising Michael addition of a malonamate ester to a linked dienone substrate that established pivotal stereocentres with excellent enantio- and complete diastereoselectivity. Furthermore, a key hemiaminal intermediate was accessed by developing an iridium-catalysed reductive cyclisation, and the scope of this transformation was explored to produce a range of bicyclic hemiaminal motifs. Once installed, the hemiaminal motif was used to initiate a biomimetic cascade to access the natural product directly in a single step. |
| first_indexed | 2024-04-09T03:57:02Z |
| format | Journal article |
| id | oxford-uuid:b24fc199-1296-4695-8dca-dea2fee10a61 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-09-25T04:02:16Z |
| publishDate | 2023 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:b24fc199-1296-4695-8dca-dea2fee10a612024-05-03T14:17:06ZEnantioselective total synthesis of (+)-incargranine A enabled by bifunctional iminophosphorane and iridium catalysisJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:b24fc199-1296-4695-8dca-dea2fee10a61EnglishSymplectic ElementsWiley2023Miller, AAMBiallas, PShennan, BDADixon, DJHerein we report the first enantioselective total synthesis of (+)-incargranine A, in nine steps. The total synthesis was enabled by an enantioselective intramolecular organocatalysed desymmetrising Michael addition of a malonamate ester to a linked dienone substrate that established pivotal stereocentres with excellent enantio- and complete diastereoselectivity. Furthermore, a key hemiaminal intermediate was accessed by developing an iridium-catalysed reductive cyclisation, and the scope of this transformation was explored to produce a range of bicyclic hemiaminal motifs. Once installed, the hemiaminal motif was used to initiate a biomimetic cascade to access the natural product directly in a single step. |
| spellingShingle | Miller, AAM Biallas, P Shennan, BDA Dixon, DJ Enantioselective total synthesis of (+)-incargranine A enabled by bifunctional iminophosphorane and iridium catalysis |
| title | Enantioselective total synthesis of (+)-incargranine A enabled by bifunctional iminophosphorane and iridium catalysis |
| title_full | Enantioselective total synthesis of (+)-incargranine A enabled by bifunctional iminophosphorane and iridium catalysis |
| title_fullStr | Enantioselective total synthesis of (+)-incargranine A enabled by bifunctional iminophosphorane and iridium catalysis |
| title_full_unstemmed | Enantioselective total synthesis of (+)-incargranine A enabled by bifunctional iminophosphorane and iridium catalysis |
| title_short | Enantioselective total synthesis of (+)-incargranine A enabled by bifunctional iminophosphorane and iridium catalysis |
| title_sort | enantioselective total synthesis of incargranine a enabled by bifunctional iminophosphorane and iridium catalysis |
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