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Catalytic asymmetric synthesis of carbocyclic C-nucleosides

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.

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Playback language: English
Abstract
Access to carbocyclic C-nucleosides (CC-Ns) is currently limited due to lengthy syntheses and poor modularity of existing methods. This paper reports a novel approach utilizing an asymmetric Suzuki-Miyaura type reaction as the key C-C bond-forming step. The process involves coupling a densely functionalized racemic bicyclic allyl chloride with heterocyclic boronic acids, followed by elaboration of the trisubstituted cyclopentenyl core to RNA analogues via a hydroborylation-homologation-oxidation sequence. This method allows for the production of 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
Tags
carbocyclic C-nucleosides
Suzuki-Miyaura reaction
C-C bond formation
RNA analogues
asymmetric synthesis
enantiomerically enriched
Showdomycin

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