title: Conception and evolution of stereocontrolled strategies toward functionalized 8-aryloctanoic acids related to the total synthesis of aliskiren.
abstract: A detailed account is given describing the approaches used toward the total synthesis of aliskiren. In particular, ring-closing metathesis with the Hoveyda-Grubbs catalyst accelerates the formation of a 9-membered lactone from an (R)-ester. The diastereomeric (S)-ester leads to the formation of dimeric dilactones, which were characterized by X-ray analysis and chemical conversions.
authors.affiliation: Department of Chemistry, Université de Montréal , CP6128 Succursale A, Centre-ville, Montréal, Quebec H3C 3J7, Canada.
authors.forename: Stephen
authors.initials: S
authors.lastname: Hanessian
authors.forename: Etienne
authors.initials: E
authors.lastname: Chénard
authors.forename: Sébastien
authors.initials: S
authors.lastname: Guesné
authors.forename: Jean-Philippe
authors.initials: JP
authors.lastname: Cusson
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002210:Caprylates / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D004952:Esters; D005650:Fumarates / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000577:Amides; D002210:Caprylates; D004952:Esters; D005650:Fumarates; D007783:Lactones; C446481:aliskiren