Faculty, Staff and Student Publications
Language
English
Publication Date
1-1-2022
Journal
Communications Chemistry
DOI
10.1038/s42004-022-00773-6
PMID
36439888
PMCID
PMC9676730
PubMedCentral® Posted Date
November 2022
PubMedCentral® Full Text Version
Post-print
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.
Keywords
Synthetic chemistry methodology, Asymmetric catalysis, Asymmetric synthesis
Published Open-Access
yes
Recommended Citation
Mishra, Sourabh; Modicom, Florian C T; Dean, Conor L; et al., "Catalytic Asymmetric Synthesis of Carbocyclic C-Nucleosides" (2022). Faculty, Staff and Student Publications. 1627.
https://digitalcommons.library.tmc.edu/uthmed_docs/1627