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Catalytic asymmetric synthesis of carbocyclic C-nucleosides
ChemistryCommunications Chemistry

Catalytic asymmetric synthesis of carbocyclic C-nucleosides

S. Mishra, F. C. T. Modicom, et al.

Discover a groundbreaking method for synthesizing carbocyclic C-nucleosides that overcomes lengthy processes and poor modularity. Researchers Sourabh Mishra, Florian C. T. Modicom, Conor L. Dean, and Stephen P. Fletcher introduce an innovative asymmetric Suzuki-Miyaura reaction, enabling the formation of diverse enantiomerically enriched CC-Ns, including a unique carbocyclic derivative of Showdomycin.... show more
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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.
Publisher
Communications Chemistry
Published On
Nov 19, 2022
Authors
Sourabh Mishra, Florian C. T. Modicom, Conor L. Dean, Stephen P. Fletcher
DOI
https://doi.org/10.1038/s42004-022-00773-6
Tags
carbocyclic C-nucleosidesSuzuki-Miyaura reactionC-C bond formationRNA analoguesasymmetric synthesisenantiomerically enrichedShowdomycin
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