Skeletal diversification by C-C cleavage to access bicyclic frameworks from a common tricyclooctane intermediate

Herein, the diversification of tricyclo[3.2.1.0(3,6)]octane scaffolds to afford diverse bicyclic scaffolds is described. The strained tricyclooctanes are prepared in two steps featuring a blue light-mediated [2+2] cycloaddition. Strategies for the cleavage of this scaffold were then explored resulting in the selective syntheses of the bicyclo[3.1.1]heptane, bicyclo[3.2.1]octane, and bicyclo[3.2.0]heptane cores. These findings may guide future studies of C-C cleavage reactions in strained carbon frameworks and their application in complex molecule synthesis.

Automated summary

This article describes the diversification of tricyclo[3.2.1.0(3,6)]octane scaffolds to synthesize diverse bicyclic scaffolds. The strained tricyclooctanes were prepared in two steps using a blue light-mediated [2+2] cycloaddition. Strategies for the cleavage of this scaffold were then explored, resulting in the selective synthesis of the bicyclo[3.1.1]heptane, bicyclo[3.2.1]octane, and bicyclo[3.2.0]heptane cores. These findings provide a guide for future studies on C-C cleavage reactions in strained carbon frameworks and their application in complex molecule synthesis.