Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library
The application of a tandem condensation/cyclisation/[3+2]-cycloaddition/elimination reaction gives an sp3-rich tricyclic pyrazoline scaffold with two ethyl esters in a single step from a simple linear starting material. The successive hydrolysis and cyclisation (with Boc anhydride) of these 3-dimen...
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| Format: | Article |
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Elsevier
2015
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| Online Access: | https://eprints.nottingham.ac.uk/46642/ |
| _version_ | 1848797375479414784 |
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| author | Storr, Thomas E. Cully, Sarah J. Rawling, Michael J. Lewis, William Hamza, Daniel Jones, Geraint Stockman, Robert A. |
| author_facet | Storr, Thomas E. Cully, Sarah J. Rawling, Michael J. Lewis, William Hamza, Daniel Jones, Geraint Stockman, Robert A. |
| author_sort | Storr, Thomas E. |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | The application of a tandem condensation/cyclisation/[3+2]-cycloaddition/elimination reaction gives an sp3-rich tricyclic pyrazoline scaffold with two ethyl esters in a single step from a simple linear starting material. The successive hydrolysis and cyclisation (with Boc anhydride) of these 3-dimensional architectures, generates unprecedented 16-membered macrocyclic bisanhydrides (characterised by XRD). Selective amidations could then be achieved by ring opening with a primary amine followed by HATU-promoted amide coupling to yield an sp3-rich natural product-like library. |
| first_indexed | 2025-11-14T20:02:53Z |
| format | Article |
| id | nottingham-46642 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T20:02:53Z |
| publishDate | 2015 |
| publisher | Elsevier |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-466422020-05-04T17:07:34Z https://eprints.nottingham.ac.uk/46642/ Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library Storr, Thomas E. Cully, Sarah J. Rawling, Michael J. Lewis, William Hamza, Daniel Jones, Geraint Stockman, Robert A. The application of a tandem condensation/cyclisation/[3+2]-cycloaddition/elimination reaction gives an sp3-rich tricyclic pyrazoline scaffold with two ethyl esters in a single step from a simple linear starting material. The successive hydrolysis and cyclisation (with Boc anhydride) of these 3-dimensional architectures, generates unprecedented 16-membered macrocyclic bisanhydrides (characterised by XRD). Selective amidations could then be achieved by ring opening with a primary amine followed by HATU-promoted amide coupling to yield an sp3-rich natural product-like library. Elsevier 2015-06-01 Article PeerReviewed Storr, Thomas E., Cully, Sarah J., Rawling, Michael J., Lewis, William, Hamza, Daniel, Jones, Geraint and Stockman, Robert A. (2015) Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library. Bioorganic and Medicinal Chemistry, 23 (11). pp. 2621-2628. ISSN 1464-3391 sp3-rich; Natural product-like; Scaffold; Cycloaddition; Two-directional; Macrocycle; Library; Tandem http://www.sciencedirect.com/science/article/pii/S0968089614009080 doi:10.1016/j.bmc.2014.12.050 doi:10.1016/j.bmc.2014.12.050 |
| spellingShingle | sp3-rich; Natural product-like; Scaffold; Cycloaddition; Two-directional; Macrocycle; Library; Tandem Storr, Thomas E. Cully, Sarah J. Rawling, Michael J. Lewis, William Hamza, Daniel Jones, Geraint Stockman, Robert A. Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library |
| title | Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library |
| title_full | Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library |
| title_fullStr | Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library |
| title_full_unstemmed | Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library |
| title_short | Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library |
| title_sort | combining two-directional synthesis and tandem reactions. part 21: exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library |
| topic | sp3-rich; Natural product-like; Scaffold; Cycloaddition; Two-directional; Macrocycle; Library; Tandem |
| url | https://eprints.nottingham.ac.uk/46642/ https://eprints.nottingham.ac.uk/46642/ https://eprints.nottingham.ac.uk/46642/ |