Resumen de Natural Product Total Synthesis in the Organic Laboratory: Total Synthesis of Caffeic Acid Phenethyl Ester (CAPE), A Potent 5-Lipoxygenase Inhibitor from Honeybee Hives
Natural products play a critical role in modern organic synthesis and learning synthetic techniques is an important component of the organic laboratory experience. In addition to traditional one-step organic synthesis laboratories, a multistep natural product synthesis is an interesting experiment to challenge students. The proposed three-step synthesis describes the total synthesis of the caffeic acid phenethyl ester (CAPE), a potent 5-lipoxygenase inhibitor from honeybee hives. Recrystallization, flash column chromatography, and circular chromatography were used for purifications. Structure verification for CAPE and all intermediates uses infrared (IR) and nuclear magnetic resonance (NMR, 1H and 13C) spectroscopy and mass spectrometry (MS). This experiment is appropriate for a second-year organic chemistry laboratory.
