ÉTUDE MÉTHODOLOGIQUE D'UNE RÉACTION DOMINO INITIÉE PAR LE TÉTRA-ACÉTATE DE PLOMB ET APPLICATION À L'APPROCHE DE LA SYNTHÈSE DES IRIDALS

Abstract : A domino reaction for generating molecular complexity which allows productive yields and an important functional group tolerance was developed. A total stereochemistry control was obtained on all introduced centers and so, two stereocontrolled adjacent quaternary centers have been synthesized.
An experimental improvement have been made to decrease the toxicity of the reaction by replacing half of the quantity of Pb(OAc)4 by less toxic PhI(OAc)2.
With this reaction, 1,2,3,4,5-stereocontroled highly functionalized cyclohexanes can be synthesized.
Iridals family (with more than 30 members) is a challenging target for the use of our domino reaction in total synthesis.
Iridals are original triterpens with important biologic activity, especially against cancer (a patent has been registered by a team from Montpellier). All iridals have in common a cyclohexane core with four contiguous stereogenic centers, two of which are adjacent quaternary centers. This dense stereochemistry makes iridals important synthetic targets.
Iridal, the mother molecule of the family, was chosen as our first target, and we have proposed a way to synthetize it. We deal with the construction of the homofarnesyl side chain in particular.
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Contributor : Guillaume Gauron <>
Submitted on : Tuesday, June 26, 2007 - 6:31:54 PM
Last modification on : Thursday, January 11, 2018 - 6:14:40 AM
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Guillaume Gauron. ÉTUDE MÉTHODOLOGIQUE D'UNE RÉACTION DOMINO INITIÉE PAR LE TÉTRA-ACÉTATE DE PLOMB ET APPLICATION À L'APPROCHE DE LA SYNTHÈSE DES IRIDALS. Autre. Université Paris Sud - Paris XI, 2007. Français. ⟨tel-00157721⟩

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