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A Straightforward Synthesis of Isoxazoline‐Based Carbocyclic Nucleosides from 1,3‐Cyclohexadiene through Nitrosocarbonyl Chemistry
Author(s) -
Quadrelli Paolo,
Mella Mariella,
Carosso Serena,
Bovio Bruna,
Caramella Pierluigi
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700569
Subject(s) - chemistry , synthon , cycloaddition , benzonitrile , stereochemistry , purine , organic chemistry , combinatorial chemistry , catalysis , enzyme
3‐Benzoyl‐2‐oxa‐3‐azabicyclo[2.2.2]oct‐5‐ene undergoes cycloaddition with benzonitrile oxide to afford a mixture of syn and anti regioisomeric cycloadducts. The anti cycloadducts were easily elaborated to stereodefined isoxazoline‐based carbocyclic aminols that serve as synthons for the linear construction of purine nucleosides. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)