A Heck-Based Strategy To Generate Anacardic Acids and Related Phenolic Lipids for Isoform-Specific Bioactivity Profiling

A synthetic strategy for phenolic lipids such as anacardic acid and ginkgolic acid derivatives using an efficient and selective redox-relay Heck reaction followed by a stereoselective olefination is reported. This approach controls both the alkene position and stereochemistry, allowing the synthesis...

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Bibliographic Details
Published in:Organic letters 2018-10, Vol.20 (19), p.6234-6238
Main Authors: Weigel, William K, Dennis, Taylor N, Kang, Amrik S, Perry, J. Jefferson P, Martin, David B. C
Format: Article
Language:English
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Summary:A synthetic strategy for phenolic lipids such as anacardic acid and ginkgolic acid derivatives using an efficient and selective redox-relay Heck reaction followed by a stereoselective olefination is reported. This approach controls both the alkene position and stereochemistry, allowing the synthesis of natural and unnatural unsaturated lipids as single isomers. By this strategy, the activities of different anacardic acid and ginkgolic acid derivatives have been examined in a matrix metalloproteinase inhibition assay.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02705