Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 15, Pages 2836-2844Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100121
Keywords
Heterocycles; Alkaloids; Cycloaddition; Rhodium; Ruthenium
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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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