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ERIC Number: EJ927036
Record Type: Journal
Publication Date: 2011-Apr
Pages: 3
Abstractor: As Provided
Reference Count: 16
ISBN: N/A
ISSN: ISSN-0021-9584
Natural Product Total Synthesis in the Organic Laboratory: Total Synthesis of Caffeic Acid Phenethyl Ester (CAPE), a Potent 5-Lipoxygenase Inhibitor from Honeybee Hives
Touaibia, Mohamed; Guay, Michel
Journal of Chemical Education, v88 n4 p473-475 Apr 2011
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, [superscript 1]H and [superscript 13]C) spectroscopy and mass spectrometry (MS). This experiment is appropriate for a second-year organic chemistry laboratory. (Contains 4 notes, 1 figure and 1 scheme.)
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A