Total Synthesis of Dodecahedrane via Carbon–Carbon Bond Forming Cascades

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Project Summary/Abstract The chemical synthesis of small molecules continues to be a vital area of research. Such efforts can lead to the development of new and improved methods, provide access to interesting or important scaffolds, and provide fundamental insight into reactivity and synthetic design that, in turn, can enable future research endeavors. This proposal is focused on achieving the total synthesis of the complex molecule dodecahedrane via the development of carbon–carbon bond forming reaction cascades. In Aim 1, a dimeric norbornyl scaffold will be prepared and utilized in an olefin metathesis isomerization reaction. This endeavor will provide access to a late-stage intermediate, while enabling the investigation and development of a unique variant of olefin methathesis for the assembly of molecular complexity. In Aim 2, a symmetrical penta-ene substrate will be synthesized and used in a unique and ambitious poly-ene cyclization, involving all five alkenes, to access dodecahedrane in the final synthetic step.