Total synthesis of oxidized welwitindolinones and (-)-N-methylwelwitindolinone C isonitrile.

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.

SUBMITTER: Quasdorf KW 

PROVIDER: S-EPMC3266994 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature