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Published on: February 16, 2018
Synthesis of Daldinans and Dynamic Stereochemistry of their Atropisomers
Hitoshi Kamauchi1, Miki Goto1, Yoshiaki Sugita1
1Department of Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1-1 Keyaki-dai, Sakado, Saitama 350-0295, Japan.
Abstract:
The synthesis of daldinans B and E (5 and 8), 3-phenyl isoindolinones isolated from Daldinia concentrica, was achieved. The conformational properties of these isoindolinones were examined using their derivatives, revealing the presence of atropisomers. The activation free-energy barrier was estimated by the variable-temperature nuclear magnetic resonance (VT-NMR) method, and density functional theory (DFT) calculations suggested that this atropisomerization was caused by equilibration via a slow rotation around the C-3-C-8 axis.
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