Stereoselective synthesis, natural occurrence and CB(2) receptor binding affinities of alkylamides from herbal medicines such as Echinacea sp |
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Authors: | Matovic N Matthias A Gertsch Jürg Raduner Stefan Bone K M Lehmann R P Devoss J J |
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Affiliation: | Chemistry, School of Molecular and Microbial Sciences, The University of Queensland, Brisbane, 4072, Australia. |
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Abstract: | A divergent synthesis of (2E,4E,8E,10E)- and (2E,4E,8E,10Z)-N-isobutyldodeca-2,4,8,10-tetraenamides from pent-4-yn-1-ol allowed identification of the (2E,4E,8E,10Z)-isomer for the first time in Echinacea species. A short, stereoselective synthesis of the (2E,4E,8E,10Z)-isomer is also described which allowed further biological evaluation of this material, and the demonstration that this isomer does not occur in Spilanthes mauritiana as previously reported. |
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