| Journal Title /掲載ジャーナル名 |
Chem |
| Publication Year and Month /掲載年月 |
June, 2025 |
| Paper Title /論文タイトル |
Facile generation of ortho-quinodimethanes toward polycyclic compounds |
| DOI /論文DOI |
10.1016/j.chempr.2025.102615 |
| Author of Waseda University /本学の著者 |
INAGAKI, Kazuya(Student, Faculty of Science and Engineering, School of Advanced Science and Engineering):Lead Author |
| Related Websites /関連Web |
– |
| Abstract /抄録 |
The streamlined synthesis of complex and functional molecules from simple and readily available starting materials has long been a fundamental goal in organic synthesis. Polycyclic carbon skeletons are particularly attractive molecular frameworks as they are prevalent in terpenoids and pharmaceuticals. Among the various strategies and reactions to access these structures,1 Diels-Alder reaction2 stands out as one of the most powerful tools, facilitating the [4+2] cycloaddition between a diene and a dienophile to rapidly form six-membered rings. Its ability to create complex cyclic structures with high regio- and stereoselectivity makes it indispensable in synthesizing natural products and bioactive compounds. Various dienes and dienophiles are known, and reaction development that leverages their exceptional reactivity is ongoing.3,4,5,6 Among these, ortho-quinodimethane (oQDM) has long been recognized as an outstanding diene (Figure 1A).7,8,9 This unique reactivity allows for the efficient construction of benzo-fused polycyclic skeletons, which are prevalent in biologically important molecules.10,11,12,13,14 However, oQDM’s high reactivity can only be unlocked by in situ generation from precursors (e.g., benzocyclobutenes and benzoheteroles) under harsh conditions.7,8,9,15,16 Furthermore, preparing these precursors is often laborious and also limits product diversity, which is a recurring issue in synthetic chemistry. A novel approach to generating oQDM from simple, readily available chemicals could address these challenges, enabling a diversity-oriented synthesis of polycyclic compounds in short sequence.17,18,19,20 Despite extensive studies on catalytic methodologies,21,22,23,24,25 these challenges have persisted for nearly 70 years since oQDM was first reported by Cava.26,27 |
