Locked nucleosides based on oxabicyclo[3.2.1]octane and oxabicyclo[2.2.1]heptane skeletons.
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[22.214.171.124(2,6)]undecane or a tricyclo[126.96.36.199(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.
Version: za2963e q8za3 q8zbc q8zca q8zd2 q8ze7 q8zf6 q8zg7