[2+2+2] Cycloadditions of Alkynylynamides – A Total Synthesis of Perlolyrine and the First Total Synthesis of “Isoperlolyrine”
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- 14 April 2011
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2011 (15) , 2836-2844
Abstract
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 β‐ and γ‐carboline cores. The choice of the catalyst strongly affects the β/γ ratio. Spectroscopic features of the γ‐isomer are distinctly different from those of the naturally occurring isoperlolyrine.Keywords
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