Total Synthesis of N-Methylwelwitindolinone D Isonitrile

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• 作者：Vikram Bhat ; Kevin M. Allan ; Viresh H. Rawal
• 刊名：Journal of the American Chemical Society
• 出版年：2011
• 出版时间：April 20, 2011
• 年：2011
• 卷：133
• 期：15
• 页码：5798-5801
• 全文大小：808K
• 年卷期：v.133,no.15(April 20, 2011)
• ISSN：1520-5126

文摘

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.