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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Catalytic asymmetric synthesis of carbocyclic C-nucleosides
Sourabh Mishra1, Florian C T Modicom1, Conor L Dean1
1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, OX1 3TA UK.
Abstract:
Access to carbocyclic C-nucleosides (CC-Ns) is currently restricted. The few methods available to make CC-Ns suffer from long syntheses and poor modularity, hindering the examination of potentially important chemical space. Here we report an approach to CC-Ns which uses an asymmetric Suzuki-Miyaura type reaction as the key C-C bond forming step. After coupling the densely functionalized racemic bicyclic allyl chloride and heterocyclic boronic acids, the trisubstituted cyclopentenyl core is elaborated to RNA analogues via a hydroborylation-homologation-oxidation sequence. We demonstrate that the approach can be used to produce a variety of enantiomerically enriched CC-Ns, including a carbocyclic derivative of Showdomycin.
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