Palladium-mediated intramolecular aryl amination on furanose derivatives: an expedient approach to the synthesis of chiral benzoxazocine derivatives and tricyclic nucleosides |
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Authors: | Neogi Arpita Majhi Tirtha Pada Mukhopadhyay Ranjan Chattopadhyay Partha |
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Institution: | Division of Medicinal Chemistry, Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Kolkata-700032, India. |
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Abstract: | Pd-catalyzed intramolecular arylamination on sugar derivatives has been accomplished by using bulky biaryl phosphine ligands. An application of this methodology on a variety of D-glucose-derived substrates, 2a-f, led to the synthesis of highly functionalized cis-fused tricyclic oxazocines, 3a-e. The products could subsequently be transformed to the optically active benzoxazocine derivative 4 and tricyclic nucleoside 6. This is the first example of the synthesis of eight-membered rings via intramolecular cycloamination of furanose derivatives, which provides a very useful method for the catalytic synthesis of medium-ring heterocycles. |
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