First Total Syntheses of TetracenomycinsC and X.
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abstract
The first total syntheses of tetracenomycinsC and X were achieved, featuring 1)preparation of a hexasubstituted naphthonitrile oxide by successive benzyne cycloadditions and an oxidative ring-opening reaction; 2)a novel ortho-quinone mono-acetal as the A-ring unit; 3)construction of three contiguous stereogenic centers by an asymmetric benzoin cyclization, an isoxazole oxidation, and a stereoselective reduction.