Synthesis of Pertyolides A, B, and C: A Synthetic Procedure to C-17-Sesquiterpenoids and a Study of Their Phytotoxic Activity
2021
Cárdenas, David M. | Rial Cumbrera, Carlos | Varela Montoya, Rosa María | González Molinillo, José María | Macías Domínguez, Francisco Antonio | Química Orgánica
C-17-sesquiterpenoids are a group of natural products that have been recently discovered. These compounds have the peculiarity of lacking the alpha,beta-methylene butyrolactone system, which is known to be quite relevant for many of the biological activities reported for sesquiterpene lactones. Unfortunately, the biological interest of C-17-sesquiterpenoids has not been studied in-depth, mainly due to the poor isolation yields in which they can be obtained from natural sources. Therefore, in order to allow a deeper study of these novel molecules, we have worked out a synthetic pathway that provides C-17-sesquiterpenoids in enough quantities from easily accessible sesquiterpene lactones to enable a more thorough investigation of their bioactivities. With this synthesis method, we have successfully synthesized, for the first time, three natural C-17-sesquiterpenoids, pertyolides A, B, and C, with good overall yields. Furthermore, we have also evaluated their phytotoxicity against etiolated wheat coleoptiles and corroborated that pertyolides B and C present strong phytotoxic activity.
Show more [+] Less [-]This research was supported by the Ministerio de Economia, Industria y Competitividad (MINEICO), Spain, AGL2017-88083-R.
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