Enoki, Winter Mushroom · 2017 · Journal Article
Medium relevanceGram-Scale, Stereoselective Synthesis and Biological Evaluation of (+)-Armillariol C.
Flammulina velutipes
Key points
- 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
Metadata-grounded summary
Citation 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.
Citation
Reddy MD, Kobori H, Mori T, Wu J, Kawagishi H, Watkins EB (2017). Gram-Scale, Stereoselective Synthesis and Biological Evaluation of (+)-Armillariol C. Journal of natural products https://doi.org/10.1021/acs.jnatprod.7b00484 PMID: 28825818
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