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1. [2+2+2] Cycloadditions of Alkynylynamides - A Total Synthesis of Perlolyrine and the First Total Synthesis of 'Isoperlolyrine'

Author

Heiner Detert, Bernhard Witulski, and Benjamin Dassonneville

Subjects
Nitrile, Chemistry, Negishi coupling, medicine.drug_class, Stereochemistry, Organic Chemistry, Total synthesis, chemistry.chemical_element, Carboxamide, Chemical synthesis, Cycloaddition, Rhodium, Catalysis, chemistry.chemical_compound, medicine, Physical and Theoretical Chemistry
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.

Published
2011
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