Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C[subscript 1]
A convergent diastereo- and enantioselective total synthesis of anticancer and antifungal macrocyclic natural product disorazole C1 is reported. The central feature of the successful route is the application of catalytic Z-selective cross-metathesis (CM). Specifically, we illustrate that catalyst-co...
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2016
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| Online Access: | http://hdl.handle.net/1721.1/103978 https://orcid.org/0000-0001-5827-3552 |
| _version_ | 1811085156351475712 |
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| author | Speed, Alexander W. H. Mann, Tyler J. O’Brien, Robert V. Schrock, Richard Royce Hoveyda, Amir H. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Speed, Alexander W. H. Mann, Tyler J. O’Brien, Robert V. Schrock, Richard Royce Hoveyda, Amir H. |
| author_sort | Speed, Alexander W. H. |
| collection | MIT |
| description | A convergent diastereo- and enantioselective total synthesis of anticancer and antifungal macrocyclic natural product disorazole C1 is reported. The central feature of the successful route is the application of catalytic Z-selective cross-metathesis (CM). Specifically, we illustrate that catalyst-controlled stereoselective CM can be performed to afford structurally complex Z-alkenyl–B(pin) as well as Z-alkenyl iodide compounds reliably, efficiently, and with high selectivity (pin = pinacolato). The resulting intermediates are then joined in a single-step operation through catalytic inter- and intramolecular cross-coupling to furnish the desired 30-membered ring macrocycle containing the critical (Z,Z,E)-triene moieties. |
| first_indexed | 2024-09-23T13:03:38Z |
| format | Article |
| id | mit-1721.1/103978 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T13:03:38Z |
| publishDate | 2016 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1039782022-09-28T11:50:19Z Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C[subscript 1] Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C1 Speed, Alexander W. H. Mann, Tyler J. O’Brien, Robert V. Schrock, Richard Royce Hoveyda, Amir H. Massachusetts Institute of Technology. Department of Chemistry Schrock, Richard Royce A convergent diastereo- and enantioselective total synthesis of anticancer and antifungal macrocyclic natural product disorazole C1 is reported. The central feature of the successful route is the application of catalytic Z-selective cross-metathesis (CM). Specifically, we illustrate that catalyst-controlled stereoselective CM can be performed to afford structurally complex Z-alkenyl–B(pin) as well as Z-alkenyl iodide compounds reliably, efficiently, and with high selectivity (pin = pinacolato). The resulting intermediates are then joined in a single-step operation through catalytic inter- and intramolecular cross-coupling to furnish the desired 30-membered ring macrocycle containing the critical (Z,Z,E)-triene moieties. National Institutes of Health (U.S.) (NIH (GM-59426) 2016-08-25T16:02:08Z 2016-08-25T16:02:08Z 2014-11 2014-09 Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/103978 Speed, Alexander W. H., Tyler J. Mann, Robert V. O’Brien, Richard R. Schrock, and Amir H. Hoveyda. "Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C[subscript 1]. Journal of the American Chemical Society 136:46 (2014), pp 16136-16139. © 2014 American Chemical Society. https://orcid.org/0000-0001-5827-3552 en_US http://dx.doi.org/10.1021/ja509973r Journal of the American Chemical Society Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) ACS |
| spellingShingle | Speed, Alexander W. H. Mann, Tyler J. O’Brien, Robert V. Schrock, Richard Royce Hoveyda, Amir H. Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C[subscript 1] |
| title | Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C[subscript 1] |
| title_full | Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C[subscript 1] |
| title_fullStr | Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C[subscript 1] |
| title_full_unstemmed | Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C[subscript 1] |
| title_short | Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C[subscript 1] |
| title_sort | catalytic z selective cross metathesis in complex molecule synthesis a convergent stereoselective route to disorazole c subscript 1 |
| url | http://hdl.handle.net/1721.1/103978 https://orcid.org/0000-0001-5827-3552 |
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