Gram-Scale, Stereoselective Synthesis and Biological Evaluation of (+)-Armillariol C
| Autor: | Takumi Mori, Hirokazu Kawagishi, Hajime Kobori, E. Blake Watkins, Jing Wu, M. Damoder Reddy |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Stereochemistry
Pharmaceutical Science 010402 general chemistry 01 natural sciences Analytical Chemistry chemistry.chemical_compound Furan Drug Discovery Organic chemistry Furans Pharmacology Biological Products Natural product Molecular Structure biology 010405 organic chemistry Organic Chemistry Enantioselective synthesis Stereoisomerism Armillaria biology.organism_classification Biological Evolution 0104 chemical sciences Complementary and alternative medicine chemistry Yield (chemistry) Molecular Medicine Stereoselectivity Enantiomer Sharpless asymmetric dihydroxylation Flammulina |
| Zdroj: | Journal of Natural Products. 80:2561-2565 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.7b00484 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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