Total Synthesis of N-Methylwelwitindolinone D Isonitrile

被引：82

作者：

Bhat, Vikram ^{[1
]}

Allan, Kevin M. ^{[1
]}

Rawal, Viresh H. ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 15期

关键词：

WELWITINDOLINONE CARBON SKELETON; MULTIPLE-DRUG RESISTANCE; C ISOTHIOCYANATE; WELWISTATIN; DIMETHYLDIOXIRANE; HAPALINDOLES; CONSTRUCTION; OXIDATION; FISCHERINDOLES; CYCLIZATION;

D O I：

10.1021/ja201834u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

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.

引用

页码：5798 / 5801

页数：4

共 45 条

[11] Straightforward enantioselective synthesis of both enantiomers of karahana lactone using a domino ring-closure sequence [J].