Gram-Scale, Stereoselective Synthesis and Biological Evaluation of (+)-Armillariol C
M Damoder Reddy1, Hajime Kobori, Takumi Mori
1Department of Pharmaceutical Sciences, College of Pharmacy, Union University , Jackson, Tennessee 38305, United States.
Abstract:
Natural products with heteroaromatic cores are ample and widespread in nature, with many compounds exhibiting promising therapeutic properties. (+)-Armillariol C (1a) is a furan-based natural product isolated from Armillaria species. Herein, we report the first enantioselective synthesis of (+)-armillariol C (1a, 79% overall yield), its enantiomer (1b), and four other analogues, on a gram-scale, using microwave-mediated, Suzuki-Miyaura cross-coupling and Sharpless asymmetric dihydroxylation reactions. Compounds were tested for plant- and mycelia-growth regulatory activity, with 1b, 7a, and 7b showing the strongest inhibitory properties in a lettuce assay and 7b and 9b inhibiting Flammulina velutipes.
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