Total synthesis of oxidized welwitindolinones and (-)-N-methylwelwitindolinone C isonitrile |
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Authors: | Quasdorf Kyle W Huters Alexander D Lodewyk Michael W Tantillo Dean J Garg Neil K |
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Affiliation: | Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA. |
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Abstract: | We report the total synthesis of (-)-N-methylwelwitindolinone C isonitrile, in addition to the total syntheses of the 3-hydroxylated welwitindolinones. Our routes to these elusive natural products feature the strategic use of a deuterium kinetic isotope effect to improve the efficiency of a late-stage nitrene insertion reaction. We also provide a computational prediction for the stereochemical configuration at C3 of the hydroxylated welwitindolinones, which was confirmed by experimental studies. |
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