Schug Janick, Morgenstern Bernd, Jauch Johann
Organic Chemistry II, Saarland University, Campus C4.2, 66123 Saarbrücken, Germany.
Org Lett. 2025 Jul 18;27(28):7719-7726. doi: 10.1021/acs.orglett.5c02569. Epub 2025 Jul 5.
First isolated from So ce 307, jerangolids are a class of natural products with high antifungal activity and minimal toxicity toward mammals. Comprised of a skipped diene substructure with a chiral center in between a δ-lactone and a pyran substituent, they present an intriguing synthetic challenge. We herein report the first synthesis of jerangolid B through a modular approach that incorporates sp-sp Stille coupling as the key step to generate the skipped diene structure. By comparing our synthetic jerangolid B to the data published in the literature, we could show that the configuration at C14 is R.
杰兰戈利德最初是从So ce 307中分离出来的，是一类具有高抗真菌活性且对哺乳动物毒性极小的天然产物。它们由一个δ-内酯和一个吡喃取代基之间带有手性中心的跳跃二烯亚结构组成，这带来了一个有趣的合成挑战。我们在此报告通过一种模块化方法首次合成杰兰戈利德B，该方法将sp-sp Stille偶联作为生成跳跃二烯结构的关键步骤。通过将我们合成的杰兰戈利德B与文献中公布的数据进行比较，我们可以证明C14位的构型为R。
