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Practical Synthesis of Enantiopure Spiro[4.4]nonane C-(2‘-Deoxy)ribonucleosides
- Source :
- The Journal of Organic Chemistry. 70:1597-1604
- Publication Year :
- 2005
- Publisher :
- American Chemical Society (ACS), 2005.
-
Abstract
- The levorotatory diol 7 has been sequentially monosilylated, dehydrated, and oxidized at the allylic methylene group to provide (+)-12. The enantiomeric dextrorotatory diol 7 has been directed down a different sequence of steps involving monosilylation, dehydration, hydroboration, Swern oxidation, and regioselective introduction of a conjugated double bond to generate (-)-33. The novel feature of these transformations is that two key deoxycarbospironucleoside intermediates of the proper absolute configuration have been made available from enantiomerically related precursors. Also reported is a highly practical and reliable means for the formation of novel 2'-deoxyribonucleosides of novel structural type from these spirocyclic cyclopentenones.
- Subjects :
- Allylic rearrangement
Deoxyribonucleosides
Stereochemistry
organic chemicals
Organic Chemistry
Diol
Molecular Conformation
Absolute configuration
Regioselectivity
Stereoisomerism
General Medicine
Chemical synthesis
chemistry.chemical_compound
Hydroboration
Enantiopure drug
chemistry
Alkanes
polycyclic compounds
Swern oxidation
Organic chemistry
Spiro Compounds
Subjects
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 70
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....15175fce209592f542d63d40f5859d75