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https://hdl.handle.net/10356/47504
Title: | Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns | Authors: | Rujee Lorpitthaya | Keywords: | DRNTU::Science::Chemistry | Issue Date: | 2010 | Source: | Rujee Lorpitthaya. (2010). Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns. Doctoral thesis, Nanyang Technological University, Singapore. | Abstract: | 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. | Description: | 268 p. | URI: | https://hdl.handle.net/10356/47504 | DOI: | 10.32657/10356/47504 | Schools: | School of Physical and Mathematical Sciences | Rights: | Nanyang Technological University | Fulltext Permission: | open | Fulltext Availability: | With Fulltext |
Appears in Collections: | SPMS Theses |
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SPMS_THESES_14.pdf | 27.89 MB | Adobe PDF | View/Open |
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