Synthèse de triènes conjugués – Approche synthétique de la wortmannilactone C et d’analogues

Abstract : The principal subject of this thesis is the synthetic approach to a natural macrolactone: wortmannilactone C. As wortmannilactone C possesses two conjugated trienic moieties, we were particularly interested in the preparation of these moieties and a method was developed to obtain conjugated trienols from conjugated iododienes and allylic alcohols under Heck-type coupling conditions. This method proved to be regioselective, stereoselective and compatible with a large variety of allylic alcohols. The coupling conditions that were developed for the formation of the trienol moiety, revealed to be ineffective to couple the complex fragments to access wortmannilactone C. Numerous other coupling conditions were tested and among them the Liebeskind conditions allowed the coupling of the fragments to access the desired conjugated trienol. However, the obtained macrolactone revealed to be a diastereomer of wortmannilactone C which was synthetized in 23 steps for the longest linear sequence.
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Damien Brandt. Synthèse de triènes conjugués – Approche synthétique de la wortmannilactone C et d’analogues. Chimie organique. Université Pierre et Marie Curie UPMC Paris VI, 2014. Français. ⟨tel-01086984⟩

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