Document type
ArticleVersion
Accepted versionPublication date
All rights reserved
Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/43283
Convenient synthesis of C75, an inhibitor of FAS and CPT1
Journal Title
Director/Tutor
Journal ISSN
Volume Title
Related resource
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.
Subject (English)
Citation
Citation
SÁNCHEZ ZARZALEJO, Carolina, et al. Convenient synthesis of C75, an inhibitor of FAS and CPT1. RSC Advances. 2013. Vol. 3, num. 6564-6571. ISSN 2046-2069. [consulted: 10 of August of 2026]. Available at: https://hdl.handle.net/2445/43283