Journal article
A cascade strategy enables a total synthesis of (±)-morphine
- Abstract:
- 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%.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 829.6KB, Terms of use)
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- Publisher copy:
- 10.1002/anie.201608526
Authors
+ Deutsche Forschungsgemeinschaft
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- Funding agency for:
- Münster, N
- Grant:
- G0601617
+ Engineering and Physical Sciences Research Council
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- Funding agency for:
- Balan, T
- Grant:
- MU 3987/1-1
- Publisher:
- Wiley
- Journal:
- Angewandte Chemie International Edition More from this journal
- Volume:
- 55
- Issue:
- 46
- Pages:
- 14306–14309
- Publication date:
- 2016-09-01
- Acceptance date:
- 2016-09-23
- DOI:
- ISSN:
-
1433-7851
- Pubs id:
-
pubs:646463
- UUID:
-
uuid:f206758b-0ec7-49ba-81d6-972348ad6e8c
- Local pid:
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pubs:646463
- Source identifiers:
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646463
- Deposit date:
-
2016-09-28
Terms of use
- Copyright holder:
- Smith et al
- Copyright date:
- 2016
- Notes:
- © 2016 The Authors. Published by Wiley-VCH Verlag GmbH and Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
- Licence:
- CC Attribution (CC BY)
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