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Issue 18, 2013
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Convenient synthesis of C75, an inhibitor of FAS and CPT1

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Abstract

C75 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.

Graphical abstract: Convenient synthesis of C75, an inhibitor of FAS and CPT1

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Article information


Submitted
20 Dec 2012
Accepted
22 Feb 2013
First published
22 Feb 2013

RSC Adv., 2013,3, 6564-6571
Article type
Paper

Convenient synthesis of C75, an inhibitor of FAS and CPT1

C. Sánchez, K. Makowski, P. Mera, J. Farràs, E. Nicolás, L. Herrero, G. Asins, D. Serra, F. G. Hegardt, X. Ariza and J. Garcia, RSC Adv., 2013, 3, 6564
DOI: 10.1039/C3RA40913A

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