Improved enantioselective synthesis of (-)-linderol A: hindered rotation about aryl-Csp(3) bond.
Fiche publication
Date publication
avril 2010
Auteurs
Membres identifiés du Cancéropôle Est :
Dr BERBER Hatice
Tous les auteurs :
Delaye PO, Lameiras P, Kervarec N, Mirand C, Berber H
Lien Pubmed
Résumé
An improved enantioselective total synthesis of (-)-linderol A has been achieved via a five-step reaction with a 21% overall yield, starting from phloroacetophenone and (-)-alpha-phellandrene, two commercially available reagents. In the diastereoselective epoxidation step, the analysis of the two endocyclic epoxide intermediates reveals a hindered sp(2)-sp(3) rotation, which results in rotational diastereoisomers.
Référence
J Org Chem. 2010 Apr 16;75(8):2501-9.