Synthetic and mechanistic apporaches to biologically potent aminoglycosides via diversified aziridination patterns.
Date of Issue2010
School of Physical and Mathematical Sciences
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.
Nanyang Technological University