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  • Title: Locked nucleosides based on oxabicyclo[3.2.1]octane and oxabicyclo[2.2.1]heptane skeletons.
    Author: Ghosh R, Maity JK, Achari B, Mandal SB.
    Journal: J Org Chem; 2010 Apr 02; 75(7):2419-22. PubMed ID: 20196557.
    Abstract:
    Intramolecular nitrone cycloaddition (INC) reaction on a d-glucose derived substrate carrying an allyl group at C-1 and an enose-nitrone at C-5 or an aldehyde-nitrone at C-1 and vinyl group at C-4 furnished a tricyclo[6.2.1.0(2,6)]undecane or a tricyclo[5.2.1.0(2,6)]decane ring structure. These tricycles were converted to bicylic nucleosides with oxabicyclo[3.2.1]octane and oxabicyclo[2.2.1]heptane rings in three steps. An oxabicyclo[3.2.1]octane ring compound could alternatively be formed by RCM reaction between C-1-allyl and C-4-vinyl moieties and transformed to nucleoside analogues through a nucleophilic substitution reaction. Participation of a neighboring benzyl ether substituent in one case paved the way for an enantiodivergent synthesis.
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