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Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate.

ABSTRACT: We report the first total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate. Our route features a number of key transformations, including an indolyne cyclization to assemble the [4.3.1]-bicyclic scaffold, as well as a late-stage intramolecular nitrene insertion to functionalize the C11 bridgehead carbon en route to the natural product.

SUBMITTER: Huters AD

PROVIDER: S-EPMC3188348 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate.

Huters Alexander D AD Quasdorf Kyle W KW Styduhar Evan D ED Garg Neil K NK

Journal of the American Chemical Society 20110811 40

We report the first total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate. Our route features a number of key transformations, including an indolyne cyclization to assemble the [4.3.1]-bicyclic scaffold, as well as a late-stage intramolecular nitrene insertion to functionalize the C11 bridgehead carbon en route to the natural product. ...[more]

PMID: 21819133

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