Total synthesis of N-methylwelwitindolinone D isonitrile |
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Authors: | Bhat Vikram Allan Kevin M Rawal Viresh H |
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Affiliation: | Department of Chemistry, The University of Chicago, Chicago, Illinois 60637, United States. |
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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. |
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