A cascade strategy enables a total synthesis of (±)-morphine
Morphine has been a target for synthetic chemists since Robinson proposed its correct structure in 1925, resulting in a large number of total syntheses of morphine alkaloids. Here we report a total synthesis of (±)-morphine that employs two key strategic cyclizations: (i) a diastereoselective...
| Main Authors: | , , , |
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| Format: | Journal article |
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Wiley
2016
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| _version_ | 1797103347612778496 |
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| author | Smith, M Chu, S Balan, T Münster, N |
| author_facet | Smith, M Chu, S Balan, T Münster, N |
| author_sort | Smith, M |
| collection | OXFORD |
| description | Morphine has been a target for synthetic chemists since Robinson proposed its correct structure in 1925, resulting in a large number of total syntheses of morphine alkaloids. Here we report a total synthesis of (±)-morphine that employs two key strategic cyclizations: (i) a diastereoselective light-mediated cyclization of an O-arylated butyrolactone to form a tricyclic cis-fused benzofuran and (ii) a cascade ene-yne-ene ring closing metathesis to forge the tetracyclic morphine core. This approach enables a short and stereoselective synthesis of morphine in an overall yield of 6.6%. |
| first_indexed | 2024-03-07T06:18:52Z |
| format | Journal article |
| id | oxford-uuid:f206758b-0ec7-49ba-81d6-972348ad6e8c |
| institution | University of Oxford |
| last_indexed | 2024-03-07T06:18:52Z |
| publishDate | 2016 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:f206758b-0ec7-49ba-81d6-972348ad6e8c2022-03-27T12:00:34ZA cascade strategy enables a total synthesis of (±)-morphineJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:f206758b-0ec7-49ba-81d6-972348ad6e8cSymplectic Elements at OxfordWiley2016Smith, MChu, SBalan, TMünster, NMorphine has been a target for synthetic chemists since Robinson proposed its correct structure in 1925, resulting in a large number of total syntheses of morphine alkaloids. Here we report a total synthesis of (±)-morphine that employs two key strategic cyclizations: (i) a diastereoselective light-mediated cyclization of an O-arylated butyrolactone to form a tricyclic cis-fused benzofuran and (ii) a cascade ene-yne-ene ring closing metathesis to forge the tetracyclic morphine core. This approach enables a short and stereoselective synthesis of morphine in an overall yield of 6.6%. |
| spellingShingle | Smith, M Chu, S Balan, T Münster, N A cascade strategy enables a total synthesis of (±)-morphine |
| title | A cascade strategy enables a total synthesis of (±)-morphine |
| title_full | A cascade strategy enables a total synthesis of (±)-morphine |
| title_fullStr | A cascade strategy enables a total synthesis of (±)-morphine |
| title_full_unstemmed | A cascade strategy enables a total synthesis of (±)-morphine |
| title_short | A cascade strategy enables a total synthesis of (±)-morphine |
| title_sort | cascade strategy enables a total synthesis of morphine |
| work_keys_str_mv | AT smithm acascadestrategyenablesatotalsynthesisofmorphine AT chus acascadestrategyenablesatotalsynthesisofmorphine AT balant acascadestrategyenablesatotalsynthesisofmorphine AT munstern acascadestrategyenablesatotalsynthesisofmorphine AT smithm cascadestrategyenablesatotalsynthesisofmorphine AT chus cascadestrategyenablesatotalsynthesisofmorphine AT balant cascadestrategyenablesatotalsynthesisofmorphine AT munstern cascadestrategyenablesatotalsynthesisofmorphine |