Platonic hydrocarbons and highly symmetric cage molecules have attracted the attention of chemists for decades. The first total synthesis of dodecahedrane, the simplest hydrocarbon with full icosahedral symmetry, more than thirty years ago was a remarkable and notorious achievement in organic chemistry. Still to date, however, the preparation of such compounds involves lengthy processes. Exploiting the elements of symmetry of the target cage molecules, as a tactic to minimize the necessary synthetic steps, is especially desirable. We noticed that building blocks containing fused five-membered rings have been the central theme of a number studies related to cage molecules. The idea of synthesizing symmetric compounds using polycyclizations, cycloadditions, and domino reactions continues to appear, even in very recent reports, but the preparation of the required substrates for such transformations has been generally unsuccessful. The present project offers an alternative strategy for the synthesis of C2-symmetric cage molecule building blocks, which is based on a bicyclic ring closure. Our approach and progress will be presented.

Bicyclic ring closure-based strategy for the synthesis of cage molecule building blocks

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