College of Plant Protection, Northwest A&F University, 3 Taicheng Road, Yangling 712100, Shaanxi, China.
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling 712100, Shaanxi, China.
J Nat Prod. 2021 Nov 26;84(11):2937-2944. doi: 10.1021/acs.jnatprod.1c00763. Epub 2021 Nov 3.
Phrymarolin II, a furofuran lignan isolated from L., features a 3,7-dioxabicyclo[3.3.0]octane skeleton. Herein, we report an alternative total synthesis of (±)-phrymarolin II (), which was performed in 9 steps from commercially available sesamol. The key steps of the synthesis included a zinc-mediated Barbier-type allylation and a copper-catalyzed anomeric -arylation. Our total synthesis allowed the synthesis of analogues of (±)-phrymarolin II. Most derivatives displayed good to excellent activity against tobacco mosaic virus (TMV). (±)-Phrymarolin II () and compounds (±)- and (±)- exhibited similar or higher activity than commercial ningnanmycin, which indicated that phrymarolin lignans are a promising new class of plant virus inhibitors.
苦马豆素 II，一种从苦马豆中分离出的呋喃木脂素，具有 3,7-二氧杂双环[3.3.0]辛烷骨架。在这里，我们报告了（±）-苦马豆素 II（）的另一种全合成方法，该方法从商业上可获得的芝麻酚出发，经过 9 步反应得到。合成的关键步骤包括锌介导的 Barbier 型烯丙基化反应和铜催化的端基异构芳基化反应。我们的全合成方法允许合成（±）-苦马豆素 II 的类似物。大多数衍生物对烟草花叶病毒（TMV）显示出良好到优异的活性。（±）-苦马豆素 II（）和化合物（±）-和（±）-表现出与商业宁南霉素相似或更高的活性，这表明苦马豆素木脂素是一类有前途的新型植物病毒抑制剂。
