Nouvelles voies d'accès à des hétérocycles substitués : par hydrogénation d'indoles, réaction de Prins, d'aza-Prins et application à la synthèse des decytospolides A et B

摘要

The heterocyclic skeleton is present in many natural and synthetic products with biological activity. The development of methods to build these patterns is an important area of research and many synthetic routes have been and are still being studied. During this work, several methods have been developed allowing access to new heterocyclic compounds: first the hydrogenation of indoles and the influence of their substitution was realised. This work allowed to develop a simple, selective and efficient method to obtain partially or fully saturated indoles. Next the development of neat and metal-free conditions for the Prins cyclization reaction gave tetrahydropyrans and was sequentially used with the Bartoli reaction. These conditions have also proved to be very efficient for sultam synthesis. Finally, a synthetic approach to decytospolides A and B was performed using the Prins cyclization reaction as key step