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A Synthetic Study of Atropurpuran: Construction of a Pentacyclic Framework by an Intramolecular Reverse-Electron-Demand Diels–Alder Reaction


  • This research was supported in part by a Grant-in-Aid for Young Scientists (B, KAKENHI no. 22790022) from the Japan Society for the Promotion of Science. We thank Prof. K. Miyamura and K. Ueji (Department of Chemistry, Tokyo University of Science) for assistance with X-ray analysis.


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Masked talent: A tetracyclo[,9.04,12]tridecane skeleton can be accessed by an intramolecular reverse-electron-demand Diels–Alder (REDDA) reaction of masked ortho-benzoquinone (MOB; see scheme). This reaction gives access to the pentacyclic framework of atropurpuran, and also enables the construction of other anti-Bredt and cage-like complex molecules.