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Total synthesis of N-methylwelwitindolinone D isonitrile.

ABSTRACT: Described is a concise total synthesis of N-methylwelwitindolinone D isonitrile, the first in a family of complex bicyclo[4.3.1]decane-containing indole alkaloids to yield to synthesis. The complete carbon core of the natural product was assembled rapidly through a Lewis acid-mediated alkylative coupling followed directly by a palladium-catalyzed enolate arylation reaction. The final ring of the pentacycle was introduced by an indole oxidation/cyclization, and the isonitrile was installed through the rearrangement of an aldehyde to an isothiocyanate followed by desulfurization.

SUBMITTER: Bhat V

PROVIDER: S-EPMC3380806 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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Total synthesis of N-methylwelwitindolinone D isonitrile.

Bhat Vikram V Allan Kevin M KM Rawal Viresh H VH

Journal of the American Chemical Society 20110329 15

Described is a concise total synthesis of N-methylwelwitindolinone D isonitrile, the first in a family of complex bicyclo[4.3.1]decane-containing indole alkaloids to yield to synthesis. The complete carbon core of the natural product was assembled rapidly through a Lewis acid-mediated alkylative coupling followed directly by a palladium-catalyzed enolate arylation reaction. The final ring of the pentacycle was introduced by an indole oxidation/cyclization, and the isonitrile was installed throug ...[more]

PMID: 21446729

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