Khan Ajmir, Rezende Fernando C
School of Packaging, Michigan State University, 448 Wilson Rd, East Lansing, Michigan 48824, United States.
Department of Fundamental Chemistry, Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes, 748, São Paulo, SP 05508-000, Brazil.
ACS Omega. 2025 Jul 25;10(30):33240-33252. doi: 10.1021/acsomega.5c03127. eCollection 2025 Aug 5.
The phenolic sesquiterpene (±)-jungianol, originally isolated from (family ), has previously been targeted through various synthetic approaches. However, none of these methods have successfully produced (±)-jungianol as the major product, largely due to difficulties in synthesizing -1,3-substituted indane frameworks. Herein, we present an annulative strategy for the total synthesis of (±)-jungianol, emphasizing several key transformations, including olefination via Wittig and Grignard reactions, hydrogenation, iodination, cross-coupling reactions, oxidation, acetylation, and hydrogenolysis of the acetylated product. Most notably, this study explores the use of a ring contraction reaction, particularly for the formation of -1,3-substituted indanes, structural motifs essential to (±)-jungianol via an environmentally friendly iodine-(III) reagent. Efforts are underway to synthesize the targeted natural product, which is just one step away from our synthesized trans-indane intermediate.
酚性倍半萜（±）-jungianol最初是从（某科）中分离出来的，此前已通过各种合成方法对其进行研究。然而，这些方法都没有成功地将（±）-jungianol作为主要产物合成出来，这主要是由于在合成-1,3-取代茚满骨架时存在困难。在此，我们提出了一种用于（±）-jungianol全合成的环化策略，重点介绍了几个关键转化步骤，包括通过维蒂希反应和格氏反应进行烯化、氢化、碘化、交叉偶联反应、氧化、乙酰化以及乙酰化产物的氢解。最值得注意的是，本研究探索了环收缩反应的应用，特别是通过一种环境友好的碘（III）试剂来形成-1,3-取代茚满，这是（±）-jungianol的关键结构基序。目前正在努力合成目标天然产物，距离我们合成的反式茚满中间体仅一步之遥。
