N-甲基威尔维啶酮 D 异腈的全合成。
Total synthesis of N-methylwelwitindolinone D isonitrile.
机构信息
Department of Chemistry, The University of Chicago, Chicago, Illinois 60637, United States.
出版信息
J Am Chem Soc. 2011 Apr 20;133(15):5798-801. doi: 10.1021/ja201834u. Epub 2011 Mar 29.
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.
摘要
本文描述了 N-甲基威尔维蒂宁酮 D 异腈的简洁全合成，这是第一个含有复杂双环[4.3.1]癸烷的吲哚生物碱家族中的成员。该天然产物的完整碳核通过路易斯酸介导的烷基化偶联快速组装，然后直接进行钯催化的烯醇化物芳基化反应。五碳环的最后一个环通过吲哚氧化/环化引入，异腈通过醛重排为异硫氰酸酯，然后脱硫来安装。
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