棕榈霉素CP17及其甲氧基类似物的全合成与抗真菌活性
Total Synthesis and Antifungal Activity of Palmarumycin CP17 and Its Methoxy Analogues.
作者信息
Wang Ruina, Liu Guoyue, Yang Mingyan, Wang Mingan, Zhou Ligang
机构信息
Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
Department of Plant Pathology, China Agricultural University, Beijing 100193, China.
出版信息
Molecules. 2016 May 7;21(5):600. doi: 10.3390/molecules21050600.
Total synthesis of naturally occurring spirobisnaphthalene palmarumycin CP17 and its methoxy analogues was first achieved through Friedel-Crafts acylation, Wolff-Kishner reduction, intramolecular cyclization, ketalization, benzylic oxidation, and demethylation using the inexpensive and readily available methoxybenzene, 1,2-dimethoxybenzene and 1,4-dimethoxybenzene and 1,8-dihydroxynaphthalene as raw materials. Demethylation with (CH₃)₃SiI at ambient temperature resulted in ring A aromatization and acetal cleavage to give rise to binaphthyl ethers. The antifungal activities of these spirobisnaphthalene derivatives were evaluated, and the results revealed that 5 and 9b exhibit EC50 values of 9.34 µg/mL and 12.35 µg/mL, respectively, against P. piricola.
首次以廉价易得的甲氧基苯、1,2 - 二甲氧基苯、1,4 - 二甲氧基苯和1,8 - 二羟基萘为原料，通过傅克酰基化、沃尔夫 - 基什纳还原、分子内环化、缩酮化、苄基氧化和脱甲基反应，实现了天然存在的螺二萘掌叶霉素CP17及其甲氧基类似物的全合成。在室温下用(CH₃)₃SiI进行脱甲基反应，导致A环芳构化和缩醛裂解，生成联萘醚。对这些螺二萘衍生物的抗真菌活性进行了评估，结果表明，5和9b对梨形孢霉的EC50值分别为9.34 µg/mL和12.35 µg/mL。
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