Please use this identifier to cite or link to this item: 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
Rights: Nanyang Technological University
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Theses

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