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Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides
A convergent, nine‐step (LLS), enantioselective synthesis of α‐cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with a chiral sulfur ylide; b) a bioinspired (3+2)‐cycloaddition of the aziridine onto an alkene; and c) ins...
| Autores principales: | , , , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
John Wiley and Sons Inc.
2018
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5817397/ https://www.ncbi.nlm.nih.gov/pubmed/29265694 http://dx.doi.org/10.1002/anie.201712065 |
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| author | Zhurakovskyi, Oleksandr Türkmen, Yunus E. Löffler, Lorenz E. Moorthie, Vijayalakshmi A. Chen, C. Chun Shaw, Michael A. Crimmin, Mark R. Ferrara, Marco Ahmad, Mushtaq Ostovar, Mehrnoosh Matlock, Johnathan V. Aggarwal, Varinder K. |
| author_facet | Zhurakovskyi, Oleksandr Türkmen, Yunus E. Löffler, Lorenz E. Moorthie, Vijayalakshmi A. Chen, C. Chun Shaw, Michael A. Crimmin, Mark R. Ferrara, Marco Ahmad, Mushtaq Ostovar, Mehrnoosh Matlock, Johnathan V. Aggarwal, Varinder K. |
| author_sort | Zhurakovskyi, Oleksandr |
| collection | PubMed |
| description | A convergent, nine‐step (LLS), enantioselective synthesis of α‐cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with a chiral sulfur ylide; b) a bioinspired (3+2)‐cycloaddition of the aziridine onto an alkene; and c) installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/N−O cleavage of a bromoisoxazole. |
| format | Online Article Text |
| id | pubmed-5817397 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2018 |
| publisher | John Wiley and Sons Inc. |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-58173972018-02-26 Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides Zhurakovskyi, Oleksandr Türkmen, Yunus E. Löffler, Lorenz E. Moorthie, Vijayalakshmi A. Chen, C. Chun Shaw, Michael A. Crimmin, Mark R. Ferrara, Marco Ahmad, Mushtaq Ostovar, Mehrnoosh Matlock, Johnathan V. Aggarwal, Varinder K. Angew Chem Int Ed Engl Communications A convergent, nine‐step (LLS), enantioselective synthesis of α‐cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with a chiral sulfur ylide; b) a bioinspired (3+2)‐cycloaddition of the aziridine onto an alkene; and c) installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/N−O cleavage of a bromoisoxazole. John Wiley and Sons Inc. 2018-01-09 2018-01-26 /pmc/articles/PMC5817397/ /pubmed/29265694 http://dx.doi.org/10.1002/anie.201712065 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
| spellingShingle | Communications Zhurakovskyi, Oleksandr Türkmen, Yunus E. Löffler, Lorenz E. Moorthie, Vijayalakshmi A. Chen, C. Chun Shaw, Michael A. Crimmin, Mark R. Ferrara, Marco Ahmad, Mushtaq Ostovar, Mehrnoosh Matlock, Johnathan V. Aggarwal, Varinder K. Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides |
| title | Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides |
| title_full | Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides |
| title_fullStr | Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides |
| title_full_unstemmed | Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides |
| title_short | Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides |
| title_sort | enantioselective synthesis of the cyclopiazonic acid family using sulfur ylides |
| topic | Communications |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5817397/ https://www.ncbi.nlm.nih.gov/pubmed/29265694 http://dx.doi.org/10.1002/anie.201712065 |
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