Practical synthesis of enantiopure spiro[4.4]nonane C-(2'-deoxy)ribonucleosides.
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.
Hartung
Ryan
R
Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA.
Paquette
Leo A
LA
D000473:Alkanes / Q000737:chemistry*; D003853:Deoxyribonucleosides / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000473:Alkanes; D003853:Deoxyribonucleosides; D013141:Spiro Compounds; C017573:nonane