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Séminaire Chimie ED459

Approaches to bioactive products from allenes

Dr. Xavier Ariza Piquer (Department of Organic Chemistry, University of Barcelona | Institut de Biomedicina de la UB, Barcelona, Spain)

publié le

Le Jeudi 11 juin 2015 à 13h45
UM FdS, salle de cours SC-20.02

Among the variety of organic functional groups, allenes have a special reactivity different from double bonds that helps to build structures with high regio- and stereoselectivity.

Our group has taken advantage of this singular reactivity to prepare 1,3-diols stereoselectively. Chiral protected 4-hydroxyallenes are added to aldehydes in a stereocontrolled manner by hydroboration to form 2-vinyl-1,3-diols that are further transformed into bioactive products such as isoavenaciolide. Similarly, nitrogen-substituted allenes allowed the stereoselective synthesis of α-quaternary amino acids and vinylsphingosine-1-phosphate derivatives that are inhibitors of lipid metabolism. The hydroboration of allenes followed by aldehyde addition was also useful for the preparation of a family of bioactive α-methylene-γ-butyrolactones.

Tetrahydro-3-benzazepines and tetrahydroisoquinolines can also be synthesized in one step from allenes and phenylethylamines or benzylamines, respectively. In this case, activation of an aromatic C-H bond directed by a primary amine followed by allene insertion and cyclization afforded the expected heterocycles.

Figure 1 (click for full view)

Contact local ICGM : Prof. Jean-Marc Campagne (équipe AM2N)

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