Starting from (1R,2S,3S,5R)- and (1S,2R,3R,5S)-6,6-dimethylspiro[bicyclo[3. 1.1]heptane-2,2′-oxiran]-3-ol (-)-8 and (+)-8, two comparative syntheses were developed for pinane-based chiral carbocyclic nucleosides. The regioselective ring opening of the spiro-oxirane ring of (-)-8 and (+)-8 with NaN3 resulted in azidodiols (-)-9 and (+)-9. Catalytic reduction of (-)-9 and (+)-9 furnished chiral aminodiols (-)-10 and (+)-10, which were transformed by linear synthesis to purine-type nucleosides 16-18 through pyrimidine intermediates. Regioselective ring opening of the oxirane ring of (-)-8 and (+)-8 resulted in adenine-, cytosine- and uracil-based carbocyclic nucleosides 19-21 in a single-step synthesis.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry