Becica Joseph, Ra Ciņš Olavs, Ivanova Marija, Jirgensons Aigars
Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, Latvia.
J Org Chem. 2023 Jul 21;88(14):10306-10309. doi: 10.1021/acs.joc.3c00952. Epub 2023 Jul 6.
Phragmalin-type limonoids are highly complex natural products based on an unusual octahydro-1-2,4-methanoindene cage. The absence of feasible routes to sufficiently functionalized methanoindene cage building blocks impedes the total synthesis of these natural products. We have developed a short and robust route to methanoindene cage compounds from the Hajos-Parrish ketone (HPK). Several stereoselective modifications of the HPK provided a substrate that underwent aldol reaction as a key step for the cage formation.
苦木素型柠檬苦素是基于一种不寻常的八氢-1,2,4-亚甲基茚笼状结构的高度复杂的天然产物。缺乏通往功能充分化的亚甲基茚笼状结构构建单元的可行路线阻碍了这些天然产物的全合成。我们已经开发出一条从哈约什-帕里什酮（HPK）出发合成亚甲基茚笼状化合物的简短而可靠的路线。对HPK进行的几种立体选择性修饰提供了一种底物，该底物经历羟醛缩合反应作为笼状结构形成的关键步骤。
