1. Practical Synthesis of Enantiopure Spiro[4.4]nonane C-(2‘-Deoxy)ribonucleosides
- Author
-
Ryan E. Hartung and Leo A. Paquette
- 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 - 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.
- Published
- 2005