[2+2+2] Cycloadditions of Alkynylynamides - A Total Synthesis of Perlolyrine and the First Total Synthesis of "Isoperlolyrine"

被引：57
作者：
Dassonneville, Benjamin [1 ]
Witulski, Bernhard [2 ]
Detert, Heiner [1 ]
机构：
[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55099 Mainz, Germany
[2] ENSICAEN, Lab Chim Mol & Thioorgan, UMR 6507, F-14050 Caen, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 15期
关键词：
Heterocycles; Alkaloids; Cycloaddition; Rhodium; Ruthenium; BETA-CARBOLINE ALKALOIDS; ONE-STEP SYNTHESIS; CATALYZED CYCLOADDITION; FLEXIBLE SYNTHESIS; GAMMA-CARBOLINE; 1,6-DIYNES; NITRILES; ALKYNES; CONSTRUCTION; PYRIDINES;
D O I：
10.1002/ejoc.201100121
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total syntheses of the carboline alkaloids perlolyrine and "isoperlolyrine" are reported. Key-steps of the syntheses are Negishi coupling reactions on alkynylynamides and their metal-catalyzed [2+2+2] cycloadditions with nitriles to form the beta- and gamma-carboline cores. The choice of the catalyst strongly affects the beta/gamma ratio. Spectroscopic features of the gamma-isomer are distinctly different from those of the naturally occurring isoperlolyrine.
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收藏
页码：2836 / 2844
页数：9
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