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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

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

Quasdorf Kyle W KW Huters Alexander D AD Lodewyk Michael W MW Tantillo Dean J DJ Garg Neil K NK

Journal of the American Chemical Society 20120111 3

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. ...[more]

PMID: 22235964

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Total Synthesis Confirms the Molecular Structure Proposed for Oxidized Levuglandin D<sub>2</sub>.

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Novel isonitrile hydratase involved in isonitrile metabolism.

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