Synthesis of toxyloxanthone B
A synthesis of the naturally occurring xanthone toxyloxanthone B is described, in which the key step is the regioselective addition of a methyl salicylate to a substituted benzyne followed by cyclization of the intermediate aryl anion to form the xanthone, the regiochemistry of the aryne addition be...
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| Format: | Article |
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Elsevier
2014
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| Online Access: | https://eprints.nottingham.ac.uk/3298/ |
| _version_ | 1848790996238729216 |
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| author | Giallombardoa, Daniele Nevin, Adam C. Lewis, William Nawrat, Christopher C. Kitson, Russell R.A. Moody, Christopher J. |
| author_facet | Giallombardoa, Daniele Nevin, Adam C. Lewis, William Nawrat, Christopher C. Kitson, Russell R.A. Moody, Christopher J. |
| author_sort | Giallombardoa, Daniele |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | A synthesis of the naturally occurring xanthone toxyloxanthone B is described, in which the key step is the regioselective addition of a methyl salicylate to a substituted benzyne followed by cyclization of the intermediate aryl anion to form the xanthone, the regiochemistry of the aryne addition being confirmed by X-ray crystallography. Subsequent introduction of the pyran ring by [3,3]-rearrangement and deprotection completed the synthesis |
| first_indexed | 2025-11-14T18:21:29Z |
| format | Article |
| id | nottingham-3298 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T18:21:29Z |
| publishDate | 2014 |
| publisher | Elsevier |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-32982020-05-04T20:16:40Z https://eprints.nottingham.ac.uk/3298/ Synthesis of toxyloxanthone B Giallombardoa, Daniele Nevin, Adam C. Lewis, William Nawrat, Christopher C. Kitson, Russell R.A. Moody, Christopher J. A synthesis of the naturally occurring xanthone toxyloxanthone B is described, in which the key step is the regioselective addition of a methyl salicylate to a substituted benzyne followed by cyclization of the intermediate aryl anion to form the xanthone, the regiochemistry of the aryne addition being confirmed by X-ray crystallography. Subsequent introduction of the pyran ring by [3,3]-rearrangement and deprotection completed the synthesis Elsevier 2014 Article PeerReviewed Giallombardoa, Daniele, Nevin, Adam C., Lewis, William, Nawrat, Christopher C., Kitson, Russell R.A. and Moody, Christopher J. (2014) Synthesis of toxyloxanthone B. Tetrahedron, 70 (6). pp. 1283-1288. ISSN 0040-4020 http://www.sciencedirect.com/science/article/pii/S0040402013019236 doi:10.1016/j.tet.2013.12.055 doi:10.1016/j.tet.2013.12.055 |
| spellingShingle | Giallombardoa, Daniele Nevin, Adam C. Lewis, William Nawrat, Christopher C. Kitson, Russell R.A. Moody, Christopher J. Synthesis of toxyloxanthone B |
| title | Synthesis of toxyloxanthone B |
| title_full | Synthesis of toxyloxanthone B |
| title_fullStr | Synthesis of toxyloxanthone B |
| title_full_unstemmed | Synthesis of toxyloxanthone B |
| title_short | Synthesis of toxyloxanthone B |
| title_sort | synthesis of toxyloxanthone b |
| url | https://eprints.nottingham.ac.uk/3298/ https://eprints.nottingham.ac.uk/3298/ https://eprints.nottingham.ac.uk/3298/ |