Guindeuil, Soizic (2006) Study of new radicalar reactions. Application to the synthesis of polycyclic compounds. PhD thesis DCSO, EP - DCSO Laboratoire de Synthèse Organique, EP/X p.289.

Alternative Locations: http://www.imprimerie.polytechnique.fr/Theses/Files/Guindeuil.pdf

Abstract

This thesis highlights, through two examples, the potential of the radical chemistry of xanthates to achieve radical reactions normally considered difficult.
After a brief introduction on chain propagation radical chemistry and more specifically the radical chemistry of xanthates, a new methodology for the synthesis of spirocyclic compounds, and in particular gamma-spirolactones, is presented. It centres around a dearomatising spirocyclisation onto a furan moiety and can be extended to the synthesis of spirolactames by replacing the furan ring with a pyrrole.
In a second part, a new approach towards the synthesis of analogs of Colchicine, a molecule isolated from Colchicum autumnale which is well known for its anticancer properties, is described. It relies upon the formation of the 7-membered B ring of this molecule in 2 or 3 steps using radical chemistry giving a quick access to a variety of analogs.

Table of content

Chapitre 1 (p 21):
Introduction à la chimie radicalaire par propagation de chaîne
Chapitre 2 (p 33):
Introduction à la chimie radicalaire des xanthates
Chapitre 3 (p 53):
Méthodes de synthèse des gamma-spirolactones
Chapitre 4 (p 77):
Synthèse de gamma-spirolactones par cyclisation sur un furane
Chapitre 5 (p 97):
La Colchicine
Chapitre 6 (p 133):
Vers la synthèse d'analogues de la Colchicine par voie radicalaire
Partie expérimentale (p 163)

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