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

Abstract

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.