title: Synthesis of some monocyclic analogues of mycophenolic acid via the Johnson ortho ester Claisen rearrangement.
abstract: The synthesis of some monocyclic analogues of mycophenolic acid in which the lactone ring has been eliminated, leaving the aromatic ring intact and the same oxygenated substituents flanking the hexenoic acid side chain with an (E)-geometry at the double bond, has been accomplished via the Johnson ortho ester Claisen rearrangement. The synthetic methodology reported here allows the preparation of mycophenolic acid analogues bearing alkyl substituents at the alpha- and beta-positions on the side chain.
authors.affiliation: Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Cuernavaca, Morelos, Mexico.
authors.forename: Ma Elena
authors.initials: ME
authors.lastname: Meza-Aviña
authors.forename: Mario
authors.initials: M
authors.lastname: Ordoñez
authors.forename: Mario
authors.initials: M
authors.lastname: Fernández-Zertuche
authors.forename: Lourdes
authors.initials: L
authors.lastname: Rodríguez-Fragoso
authors.forename: Jorge
authors.initials: J
authors.lastname: Reyes-Esparza
authors.forename: Abril A Martínez
authors.initials: AA
authors.lastname: de Los Ríos-Corsino
mesh_terms: D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D003500:Cyclization; D004952:Esters / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D009173:Mycophenolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity
chemical_list: D004952:Esters; D009173:Mycophenolic Acid