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...
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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 |
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