期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2011, 期 15, 页码 2836-2844出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100121
关键词
Heterocycles; Alkaloids; Cycloaddition; Rhodium; Ruthenium
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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