Generation of a heteropolycyclic and sp3-rich scaffold for library synthesis from a highly diastereoselective Petasis/Diels–Alder and ROM–RCM reaction sequence
Efficient access to diverse screening compounds with desirable, lead-like properties can be a bottleneck in early drug discovery and chemical biology. Herein we present an efficient, rapid route to three structurally distinct classes of compounds (A–C) from a single precursor, which in turn is avail...
| Main Authors: | , , , , , , , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2021
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/150792 |
| _version_ | 1826110932130988032 |
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| author | Flagstad, Thomas Azevedo, Carlos M. G. Troelsen, Nikolaj S. Min, Geanna K. Macé, Yohan Willaume, Anthony Guilleux, Rachel Velay, Mélanie Bonnet, Karine Morgentin, Remy Nielsen, Thomas E. Clausen, Mads H. |
| author2 | Singapore Centre for Environmental Life Sciences and Engineering |
| author_facet | Singapore Centre for Environmental Life Sciences and Engineering Flagstad, Thomas Azevedo, Carlos M. G. Troelsen, Nikolaj S. Min, Geanna K. Macé, Yohan Willaume, Anthony Guilleux, Rachel Velay, Mélanie Bonnet, Karine Morgentin, Remy Nielsen, Thomas E. Clausen, Mads H. |
| author_sort | Flagstad, Thomas |
| collection | NTU |
| description | Efficient access to diverse screening compounds with desirable, lead-like properties can be a bottleneck in early drug discovery and chemical biology. Herein we present an efficient, rapid route to three structurally distinct classes of compounds (A–C) from a single precursor, which in turn is available through a one-pot Petasis 3-component reaction/Diels–Alder cascade reaction. We demonstrate the versatility of the approach through the synthesis of 35 exemplary compounds from the three classes, as well as by the production of 2188 final compounds, which have been included in the Joint European Compound Library of the European Lead Factory. |
| first_indexed | 2024-10-01T02:42:16Z |
| format | Journal Article |
| id | ntu-10356/150792 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T02:42:16Z |
| publishDate | 2021 |
| record_format | dspace |
| spelling | ntu-10356/1507922021-06-08T08:34:53Z Generation of a heteropolycyclic and sp3-rich scaffold for library synthesis from a highly diastereoselective Petasis/Diels–Alder and ROM–RCM reaction sequence Flagstad, Thomas Azevedo, Carlos M. G. Troelsen, Nikolaj S. Min, Geanna K. Macé, Yohan Willaume, Anthony Guilleux, Rachel Velay, Mélanie Bonnet, Karine Morgentin, Remy Nielsen, Thomas E. Clausen, Mads H. Singapore Centre for Environmental Life Sciences and Engineering Science::Chemistry Drug Discovery Heterocycles Efficient access to diverse screening compounds with desirable, lead-like properties can be a bottleneck in early drug discovery and chemical biology. Herein we present an efficient, rapid route to three structurally distinct classes of compounds (A–C) from a single precursor, which in turn is available through a one-pot Petasis 3-component reaction/Diels–Alder cascade reaction. We demonstrate the versatility of the approach through the synthesis of 35 exemplary compounds from the three classes, as well as by the production of 2188 final compounds, which have been included in the Joint European Compound Library of the European Lead Factory. 2021-06-08T08:34:52Z 2021-06-08T08:34:52Z 2019 Journal Article Flagstad, T., Azevedo, C. M. G., Troelsen, N. S., Min, G. K., Macé, Y., Willaume, A., Guilleux, R., Velay, M., Bonnet, K., Morgentin, R., Nielsen, T. E. & Clausen, M. H. (2019). Generation of a heteropolycyclic and sp3-rich scaffold for library synthesis from a highly diastereoselective Petasis/Diels–Alder and ROM–RCM reaction sequence. European Journal of Organic Chemistry, 2019(5), 1061-1076. https://dx.doi.org/10.1002/ejoc.201801551 1434-193X 0000-0002-5513-5549 0000-0001-9649-1729 https://hdl.handle.net/10356/150792 10.1002/ejoc.201801551 2-s2.0-85058842528 5 2019 1061 1076 en European Journal of Organic Chemistry © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. All rights reserved. |
| spellingShingle | Science::Chemistry Drug Discovery Heterocycles Flagstad, Thomas Azevedo, Carlos M. G. Troelsen, Nikolaj S. Min, Geanna K. Macé, Yohan Willaume, Anthony Guilleux, Rachel Velay, Mélanie Bonnet, Karine Morgentin, Remy Nielsen, Thomas E. Clausen, Mads H. Generation of a heteropolycyclic and sp3-rich scaffold for library synthesis from a highly diastereoselective Petasis/Diels–Alder and ROM–RCM reaction sequence |
| title | Generation of a heteropolycyclic and sp3-rich scaffold for library synthesis from a highly diastereoselective Petasis/Diels–Alder and ROM–RCM reaction sequence |
| title_full | Generation of a heteropolycyclic and sp3-rich scaffold for library synthesis from a highly diastereoselective Petasis/Diels–Alder and ROM–RCM reaction sequence |
| title_fullStr | Generation of a heteropolycyclic and sp3-rich scaffold for library synthesis from a highly diastereoselective Petasis/Diels–Alder and ROM–RCM reaction sequence |
| title_full_unstemmed | Generation of a heteropolycyclic and sp3-rich scaffold for library synthesis from a highly diastereoselective Petasis/Diels–Alder and ROM–RCM reaction sequence |
| title_short | Generation of a heteropolycyclic and sp3-rich scaffold for library synthesis from a highly diastereoselective Petasis/Diels–Alder and ROM–RCM reaction sequence |
| title_sort | generation of a heteropolycyclic and sp3 rich scaffold for library synthesis from a highly diastereoselective petasis diels alder and rom rcm reaction sequence |
| topic | Science::Chemistry Drug Discovery Heterocycles |
| url | https://hdl.handle.net/10356/150792 |
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