Catalytic asymmetric synthesis of carbocyclic C-nucleosides

Journal article

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

Authors: Mishra, S; Modicom, FCT; Dean, CL; Fletcher, SP

• Publication status: Published
• Peer review status: Peer reviewed
• Publisher: Nature Research
• Journal: Communications Chemistry
• Volume: 5
• Issue: 1
• Pages: 154-154
• Article number: 154
• Publication date: 2022-11-19
• DOI: 10.1038/s42004-022-00773-6
• EISSN: 2399-3669
• ISSN: 2399-3669
• Language: English
• Keywords: Modularity (biology); Stereochemistry; Biology; Organic chemistry; Catalysis; Enantioselective synthesis; Chemistry; Derivative (finance); Boronic acid; Bicyclic molecule; Combinatorial chemistry