The Computational Examination of the Stereoselective Radical Cyclization of the Complex Molecules

Abstract

The stereoselectivity of the 7-endo radical cyclization in the syntheses of the complex terpenoids, resiniferatoxin and the model compound of puberulin C, was computationally examined. The DFT calculation of the transition states of the radical cyclizations provided the reasonable explanation for the stereoselective formation of the desired compounds. In the synthesis of the model compound of puberuline C, the energy profile of the radical reaction illustrated the favorable cascade process from the tricyclic intermediate to the pentacyclic compound.