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Dimakos, Victoria; Gorelik, Daniel; Su, Hsin Y; Garrett, Graham E; Hughes, Gregory; Shibayama, Hiromitsu; Taylor, Mark S
Chemical science, 01/2020, Letnik: 11, Številka: 6Journal Article
In the presence of an arylboronic acid and a hydrogen atom transfer mediator under photoredox conditions, furanoside derivatives undergo site-selective redox isomerizations to 2-keto-3-deoxyfuranosides. Experimental evidence and computational modeling suggest that the transformation takes place by abstraction of the hydrogen atom from the 2-position of the furanoside-derived arylboronic ester, followed by C3-O bond cleavage via spin-center shift. This mechanism is reminiscent of the currently accepted pathway for the formation of 3′-ketodeoxynucleotides by ribonucleotide reductase enzymes. The combined action of boronic acid, photoredox catalyst and hydrogen atom transfer mediator enables the transformation of furanosides to 2-keto-3-deoxyfuranosides, a synthetic analog of the process catalyzed by the ribonucleotide reductase enzymes.
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