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Synfacts 2006(3): 0186-0186
DOI: 10.1055/s-2006-931927
DOI: 10.1055/s-2006-931927
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthesis of (-)-Oleocanthal
A. B. Smith III*, Q. Han, P. A. S. Breslin, G. K. Beauchamp
University of Pennsylvania, Philadelphia, USA
Further Information
Publication History
Publication Date:
21 February 2006 (online)
Significance
(-)-Oleocanthal, an irritant found in extra virgin olive oil, is an anti-inflammatory agent similar in potency to ibuprofen and an anti-oxidant similar in potency to α-tocopherol. The absolute configuration was established by total synthesis of both enantiomers from Δ-ribose (12 steps, 7% overall). Both enantiomers have similar potency.