AI Article Synopsis
- - Current methods for accessing carbocyclic C-nucleosides (CC-Ns) are limited, featuring long synthesis processes and poor versatility, which restricts research into their potential applications.
- - The new approach introduced relies on an asymmetric Suzuki-Miyaura reaction for creating C-C bonds, allowing for more efficient synthesis of CC-Ns.
- - This method successfully produces various enantiomerically enriched CC-Ns, including a carbocyclic version of Showdomycin, expanding the toolkit for researchers investigating these compounds.
Article 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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|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9676730 | PMC |
| http://dx.doi.org/10.1038/s42004-022-00773-6 | DOI Listing |
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