Selective Synthesis of 1,3-Substituted Cuneanes: En Route to Potent Bioisosteres of m-Substituted Benzenes

10 May 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


We herein disclose a method to obtain 1,3-substituted cuneane by selective isomerization of 1,4-substituted cubanes. The electronic property of the substituent strongly affects the isomerization ratio of 1,3-substituted cuneane and 2,6-substituted cuneane. Based on structural similarity, we considered that 1,3-substituted cuneane would be a bioisostere of m-substituted benzene. The synthesis of a cuneane analog of pharmaceuticals having m-substituted benzene moiety and its biological evalu-ation are also described.




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