Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns
268 p.
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| Other Authors: | |
| Format: | Thesis |
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2011
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| Online Access: | https://hdl.handle.net/10356/47504 |
| _version_ | 1826124122601553920 |
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| author | Rujee Lorpitthaya |
| author2 | Liu Xuewei |
| author_facet | Liu Xuewei Rujee Lorpitthaya |
| author_sort | Rujee Lorpitthaya |
| collection | NTU |
| description | 268 p. |
| first_indexed | 2024-10-01T06:15:30Z |
| format | Thesis |
| id | ntu-10356/47504 |
| institution | Nanyang Technological University |
| last_indexed | 2024-10-01T06:15:30Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | ntu-10356/475042023-02-28T23:49:16Z Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns Rujee Lorpitthaya Liu Xuewei School of Physical and Mathematical Sciences DRNTU::Science::Chemistry 268 p. The flexible installation of a sulfamate ester group on different positions of the glycal scaffold has been highlighted to be a new concept for synthesizing a- and P-aminoglycosides. The methodology incorporated three relevant steps: 1) the introduction of the sulfamate ester on the C3, C4, or C6 position of the glycal, 2) the intramolecular rhodium-catalyzed aziridination, and 3) regio- and stereoselective ring-opening of aziridines with readily available nucleophiles. With this rational design of substrates, the possibility, reactivity and limitation of forming aziridine-ring intermediates from 1, 2, and 3 have been performed based on the results from experimental observations and DFT calculations. DOCTOR OF PHILOSOPHY (SPMS) 2011-12-27T08:30:57Z 2011-12-27T08:30:57Z 2010 2010 Thesis Rujee Lorpitthaya. (2010). Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/47504 10.32657/10356/47504 Nanyang Technological University application/pdf |
| spellingShingle | DRNTU::Science::Chemistry Rujee Lorpitthaya Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| title | Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| title_full | Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| title_fullStr | Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| title_full_unstemmed | Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| title_short | Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| title_sort | synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| topic | DRNTU::Science::Chemistry |
| url | https://hdl.handle.net/10356/47504 |
| work_keys_str_mv | AT rujeelorpitthaya syntheticandmechanisticapproachestobiologicallypotentaminoglycosidesviadiversifiedaziridinationpatterns |