Catalytic, Asymmetric Indolizidinone Aza-Quaternary Stereocenter Synthesis: Expedient Synthesis of the Cylindricine Alkaloid Core

被引：29

作者：

Dalton, Derek M. ^{[1
]}

Rovis, Tomislav ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 10期

关键词：

TRICYCLIC MARINE ALKALOIDS; 2+2+2 CYCLOADDITION; ALKENYL ISOCYANATES; ENANTIOSELECTIVE SYNTHESIS; TERMINAL ALKYNES; AMPHIBIAN SKIN; (+)-CYLINDRICINE-C; COMPLEXES; CYCLIZATION; (+/-)-CYLINDRICINES;

D O I：

10.1021/ol400529k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Rh(I)center dot CKphos catalyzed [2 + 2 + 2] cycloaddition of 1,1-disubstituted alkenyl isocyanates and alkyl alkynes selectively forms previously inaccessible vinylogous amide indolizidinone cycloadducts, establishing an aza-quaternery stereocenter with excellent enantioselectivities (up to 98% ee). This advance enables a seven step catalytic, asymmetric synthesis of the tricyclic core of the cylindricine alkaloids with excellent control of product selectivity as well as regio- and enantioselectivity.

引用

页码：2346 / 2349

页数：4

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