Total synthesis of N-methylwelwitindolinone D isonitrile

作者:Bhat V; Allan K M; Rawal V H*
来源:Journal of the American Chemical Society, 2011, 133(15): 5798-5801.
DOI:10.1021/ja201834u

摘要

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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