Synthesis of some monocyclic analogues of mycophenolic acid via the Johnson ortho ester Claisen rearrangement.
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.
Meza-Aviña
Ma Elena
ME
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Cuernavaca, Morelos, Mexico.
Ordoñez
Mario
M
Fernández-Zertuche
Mario
M
Rodríguez-Fragoso
Lourdes
L
Reyes-Esparza
Jorge
J
de Los Ríos-Corsino
Abril A Martínez
AA
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
D004952:Esters; D009173:Mycophenolic Acid