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Recent Advances in Aryl C-Glycoside Synthesis

[ Vol. 5 , Issue. 14 ]

Author(s):

David Y. W. Lee and Minsheng He   Pages 1333 - 1350 ( 18 )

Abstract:


Aryl C-glycosides are stable analogs of the corresponding O-glycosides. Because of their favorable pharmacological profiles attributed primarily to the C-glycosyl moiety, aryl C-glycosides have gained increasing popularity as drug candidates. In this review we focus on the synthesis of aryl C-glycosides including puerarin and kendomycin. This review is organized based on the type of chemistry used in the assembly of the C-glycosides with the following sub-sections: electrophilic reaction, cross-coupling reaction, free radical reaction, cyclization, intramolecular OC rearrangement, umpolung, and miscellaneous reactions.

Keywords:

de-O-methylation, Glycosyl halides, Lactones, Cyclization, intramolecular tether approach, umpolung

Affiliation:

Bioorganic and Natural ProductsLaboratory, McLean Hospital, Harvard Medical School, 115 Mill Street,Belmont, MA 02478.



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