Concise synthesis of bicyclic pyridinol antioxidants |
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Authors: | Lu Jun Cai Xiaoqing Hecht Sidney M |
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Affiliation: | Center for BioEnergetics, The Biodesign Institute, and Department of Chemistry, Arizona State University, Tempe, Arizona 85287, United States. |
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Abstract: | The recently reported bicyclic pyridinols 1 and 2 are highly effective antioxidants exhibiting 88- and 28-fold greater potency, respectively, than α-tocopherol when assayed for their ability to suppress the autoxidation of methyl linoleate. Described herein is a short, economical, and scalable strategy for the synthesis of this novel group of antioxidants, as well as analogues 3-6. Key reactions involved the cyclocondensation reaction of lactam acetals with enaminone 7 and selective functionalizaton of the heterocyclic systems. |
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