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Development of a Generic Stereocontrolled Pathway to Fully Hydroxylated Spirocarbocyclic Nucleosides as a Prelude to RNA Targeting
- Source :
- Synthesis. :3209-3218
- Publication Year :
- 2005
- Publisher :
- Georg Thieme Verlag KG, 2005.
-
Abstract
- Osmylation of the enantiopure conjugated enones 4 and 15 proceeded predominantly or exclusively from the α-face to give the 2',3'-diols 6 and 16. Ensuing conversion into the acetonide allowed for sequential stereocontrolled reduction with L-Selectride, and esterification with triflic anhydride was utilized to form triflates 11 and 19. The heightened electrophilicity of these intermediates made possible S N 2 displacements with several nucleobases as promoted with potassium hydride in N,N-dimethylformamide at room temperature. Suitable deprotection measures led to the targeted compounds.
Details
- ISSN :
- 1437210X and 00397881
- Database :
- OpenAIRE
- Journal :
- Synthesis
- Accession number :
- edsair.doi...........694d9caadd0bccb9f93b84d454ea4aad