Abstract
C-Glycosylphenols and -polyphenols occur widely in nature and present a variety of biological properties, namely antitumor, antibacterial and antidiabetic activities. Synthetic access to such structures relies mainly on efficient methodologies for phenols C-glycosylation. In the past few years major advances have been described addressing the use of Fries rearrangement to obtain a diversity of C-glycosyl compounds. Herein we survey the glycosyl donors and the activators used for this reaction, covering both early work and recent developments in the area. Reaction mechanism and reaction outcome control, aiming at regio- and stereoselectivity are also discussed.
Keywords: Phenols C-glycosylation, Fries-type rearrangement, activator, C-Glycosylphenols, Cglycosylation, stereoselectivity, antibiotics pluramycins, samarium iodide, boron trifluoride, oxonium ion, sugar trichloroacetimidates, Tin Chloride, ribofuranosyl fluoride, vineomycin B2, naphthols, Glycosyl acetates, rhamnosyl acetate, dichloromethane, pluramycins, resorcinol, mannosyl fluoride, Montmorillonite K-10
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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