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Catalytic asymmetric synthesis of carbocyclic C-nucleosides.

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.

SUBMITTER: Mishra S

PROVIDER: S-EPMC9676730 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature

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Catalytic asymmetric synthesis of carbocyclic C-nucleosides.

Mishra Sourabh S Modicom Florian C T FCT Dean Conor L CL Fletcher Stephen P SP

Communications chemistry 20221119 1

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 elabo ...[more]

PMID: 36439888

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