Abstract
We present here a synthetic path to produce, exclusively, 8,9-epoxy-limonene in 75% overall yields. We developed a three step synthetic route. First, the 1,2-double bond of limonene was protected by the formation of the bromo-methyl-ether by cohalogenation with NBS in MeOH. Then, this product was oxidized by m-chloro-perbenzoic acid to give the corresponding epoxides. Finally, the 1,2-double bond was restored by a reaction with NH4Cl/Zn leading to 8,9-epoxy-limonene. The great advantage of this methodology is that the intermediate purification steps are not necessary.
Acknowledgment
We thank CNPq and CAPES for financial support, and Claudia Moraes de Rezende for the mass analyses. We thank Flavia M. da Silva for helpful discussions.