ヌクレオシドの糖部分における炭素-炭素結合の構築 : 不飽和糖ヌクレオシドの有用性

概要

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Unsaturated-sugar nucleosides have been shown to serve as versatile substrates for constructing C-C bond at the sugar portion. Various types of appropriate reactions were adopted to 1, 2-, 2, 3-, 3, 4-, and 4, 5-unsaturated derivatives. These are electrophilic addition followed by substitution with organosilicon and organoaluminum reagents, radical-mediated 1, 2-acyloxy migration of the adducts, nucleophilic addition of benzenethiolate followed by radical substitution, aldol reaction of an enol ester, Pd-catalyzed cross-coupling and halogen-lithium exchange reactions of nucleosidic vinyl bromides, S<SUB>N</SUB>2 reaction, addition reaction of carbon radicals, and epoxide ring opening with organometallic reagents. Consequently, C-C bond formation at the 1-, 2-, 3-, 4-, and 5-positions of nucleoside became possible.
社団法人有機合成化学協会の論文
2003-10-01