Gram-Scale, Stereoselective Synthesis and Biological Evaluation of (+)-Armillariol C,Journal of Natural Products

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Gram-Scale, Stereoselective Synthesis and Biological Evaluation of (+)-Armillariol C
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-08-21 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00484
M. Damoder Reddy ₁ , Hajime Kobori , Takumi Mori , Jing Wu , Hirokazu Kawagishi , E. Blake Watkins ₁

Affiliation

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.

中文翻译：

（+）-Armillariol C的克级，立体选择性合成和生物学评估

具有杂芳族核心的天然产物在自然界中是丰富而广泛的，许多化合物表现出有希望的治疗特性。（+）- Armillariol C（1a）是一种从呋喃菌属物种中分离出来的基于呋喃的天然产物。在此，我们报道了使用微波介导的Suzuki-Miyaura杂交技术以克为单位的（+）-蜜环丙醇C（1a，总收率79％），其对映异构体（1b）和其他四个类似物的首次对映选择性合成。偶联和Sharpless不对称二羟基化反应。测试了化合物对植物和菌丝体生长的调节活性，分别为1b，7a和7b在生菜试验中表现出最强的抑制作用，并抑制7b和9b的金针菇。

更新日期：2017-08-21

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