Synthetic studies on the application of the intramolecular azide-alkene 1,3-dipolar cycloaddition reaction in the construction of the core structure of complex alkaloids

Synthesis of the core skeletons of the polycyclic alkaloids lycopodine and porantherine has been accomplished employing as a key step an Intramolecular Azide-Olefin Cycloaddition reaction (IAOC)/enamine addition/Mannich cascade reaction. Applying this methodology, the first synthesis of C-15-desmethyl lycopodine has been developed. (C) 2016 Elsevier Ltd. All rights reserved.