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