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棕榈霉素 B 的全合成及结构修正。

Total Synthesis and Structure Revision of Palmarumycin B.

出版信息

J Nat Prod. 2018 Aug 24;81(8):1803-1809. doi: 10.1021/acs.jnatprod.8b00258. Epub 2018 Aug 13.

Abstract

Palmarumycin B and its regioisomer were synthesized via 7- and 13-step routes using 2-chlorophenol and 4-chlorophenyl methyl ether as the starting materials in overall yields of 2.7% and 12%, respectively. Their structures were characterized by H and C NMR, HRESIMS, and X-ray diffraction data. The structure of palmarumycin B was revised as 6-chloropalmarumycin CP. The bioassay results showed that the larvicidal activity of palmarumycin B with an LC value of 32.7 μM was significantly higher than that of its 8-chloro isomer, with an LC value of 227.3 μM.

摘要

掌霉素 B 及其区域异构体分别通过 7 步和 13 步路线,以 2-氯苯酚和 4-氯苯甲醚为起始原料合成,总收率分别为 2.7%和 12%。它们的结构通过 H 和 C NMR、HRESIMS 和 X 射线衍射数据进行了表征。掌霉素 B 的结构被修订为 6-氯掌霉素 CP。生物测定结果表明,LC 值为 32.7 μM 的掌霉素 B 的杀虫活性明显高于其 8-氯异构体(LC 值为 227.3 μM)。

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