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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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Title Palladium-Mediated Intramolecular Aryl Amination on Furanose Derivatives: An Expedient Approach to the Synthesis of Chiral Benzoxazocine Derivatives and Tricyclic
Nucleosides
 
Creator Neogi, Arpita
Majhi, Tirtha Pada
Mukhopadhyay, Ranjan
Chattopadhyay, Partha
 
Subject Chemistry
 
Description 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
 
Date 2006
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/400/1/JOURNAL_OF_ORGANIC_CHEMISTRY%2C__71(_8)%2C_3291%2D3294[102].pdf
Neogi, Arpita and Majhi, Tirtha Pada and Mukhopadhyay, Ranjan and Chattopadhyay, Partha (2006) Palladium-Mediated Intramolecular Aryl Amination on Furanose Derivatives: An Expedient Approach to the Synthesis of Chiral Benzoxazocine Derivatives and Tricyclic Nucleosides. The Journal of Organic Chemistry, 71. pp. 3291-3294.
 
Relation http://dx.doi.org/10.1021/jo052420i CCC: $33.50
http://www.eprints.iicb.res.in/400/