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First Total Syntheses of Tetracenomycins C and X
Shogo Sato1, Keiichiro Sakata1, Yoshimitsu Hashimoto1,2
1Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
Abstract:
The first total syntheses of tetracenomycins C 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.
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