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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Practical synthesis of enantiopure spiro[4.4]nonane C-(2'-deoxy)ribonucleosides
1Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA.
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.
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