We synthesized fluoro- and hydroxy-containing octahydro-2H-chromenes by the Prins reaction starting from a monoterpenoid (–)-isopulegol and a wide range of aromatic aldehydes in the presence of the BF₃∙Et₂O/H₂O system acting as both an acid catalyst and a fluorine source. Activity of the produced compounds against the influenza A/Puerto Rico/8/34 (H1N1) virus was studied. The highest activity was demonstrated by fluoro- (11i) and hydroxy-containing (10i) derivatives of 2,4,6-trimethoxybenzaldehyde. The most pronounced virus-inhibiting effect of compounds 10i and 11i was observed at an early stage of infection. These compounds were supposed to be capable of binding to viral hemagglutinin, which is an agreement with data on the effect of compounds 10i and 11i on the viral fusogenic activity as well as by molecular docking studies.

在BF ₃ ∙Et ₂ O / H ₂ O系统存在下，我们通过Prins反应从单萜（–）-异胡薄荷醇和各种芳香醛开始合成了含氟和羟基的octahydro-2 H-色烯。同时充当酸催化剂和氟源。研究了所产生的化合物对甲型流感/波多黎各/ 8/34（H1N1）病毒的活性。2,4,6-三甲氧基苯甲醛的含氟（11i）和含羟基（10i）衍生物显示出最高的活性。化合物10i和11i最明显的病毒抑制作用在感染的早期阶段被观察到。假定这些化合物能够结合病毒血凝素，这与化合物10i和11i对病毒融合活性的作用以及分子对接研究的数据一致。