1218919-06-2Relevant academic research and scientific papers
Locked nucleosides based on oxabicyclo[3.2.1]octane and oxabicyclo[2.2.1]heptane skeletons
Ghosh, Ramprasad,Maity, Joy Krishna,Achari, Basudeb,Mandal, Sukhendu B.
supporting information; experimental part, p. 2419 - 2422 (2010/07/02)
(Figure Presented) Intramolecular nitrone cycloaddition (INC) reaction on a D-glucose derived substrate carrying an allyl group at C-I and an enose-nitrone at C-5 or an aldehyde-nitrone at C-I and vinyl group at C-4 furnished a tricyclo[6.2.1.02,6]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.
