Sánchez Zarzalejo, CarolinaMakowski, KamilMera Nanín, PaulaFarràs i Soler, JaumeNicolás Galindo, ErnestoHerrero Rodríguez, LauraAsins Muñoz, GuillerminaSerra i Cucurull, DolorsGarcía Hegardt, FaustoAriza Piquer, XavierGarcía Gómez, Jordi2013-05-102014-04-172013-04-172046-2069https://hdl.handle.net/2445/43283C75 is a synthetic racemic α-methylene-γ-butyrolactone exhibiting anti-tumoral properties in vitro and in vivo as well as inducing hypophagia and weight loss in rodents. These interesting properties are thought to be a consequence of the inhibition of the key enzymes FAS and CPT1 involved in lipid metabolism. The need for larger amounts of this compound for biological evaluation prompted us to develop a convenient and reliable route to multigram quantities of C75 from easily available ethyl penta-3,4-dienoate 6. A recently described protocol for the addition of 6 to a mixture of dicyclohexylborane and nonanal followed by acidic treatment of the crude afforded lactone 8, as a mixture of cis and trans isomers, in good yield. The DBU-catalyzed isomerization of the methyl esters 9 arising from 8 gave a 10:1 trans/cis mixture from which the trans isomer was isolated and easily transformed into C75. The temporary transformation of C75 into a phenylseleno ether derivative makes its purification, manipulation and storage easier.18 p.application/pdfeng(c) Sánchez Zarzalejo, Carolina et al., 2013Inhibidors enzimàticsTrastorns del metabolisme dels lípidsCàncerDiabetisAprimamentEnzyme inhibitorsLipid metabolism disordersCancerDiabetesWeight lossinfo:eu-repo/semantics/article6205552013-05-07info:eu-repo/semantics/openAccess