Carbocyclic Ring Closure of Aryl C-Glycosides Promoted by Fluoroboric Acid
- 22 June 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (14), 9339-9346
- https://doi.org/10.1021/acs.joc.0c00784
Abstract
A novel transformation from rhamnose-type C-glycosides to 2-cyclopentenones is described. With the promotion of fluoroboric acid, C-glycosides underwent ring opening and subsequent Nazarov cyclization to afford 2-cyclopentenones in good to excellent yields. The solvent and the concentration of acid are crucial to the yield of this transformation.Keywords
Funding Information
- National Natural Science Foundation of China (21572012, 21772006, 91853122)
- State Key Laboratory of Drug Research (SIMM1803KF-02)
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