A number of adamantane-based small molecules are believed to be useful in the treatment of a variety of diseases, ranging from neurodegenerative diseases such as Parkinson's and Alzheimer's disease, to viral diseases such as HIV. In addition, the high level of symmetry and the peculiar non-planar geometry of the bridgehead adamantyl cation have fascinated chemists since the discovery of the adamantane core in 1933. We thus desired to probe the ability to efficiently construct substituted adamantanones, potential precursors to the corresponding adamantanes. Trifluoromethanesulfonic acid facilitates formation of the adamantanone core from dimethylenebicyclo[3.3.1]nonanone. The resulting adamantyl cation may be trapped with a variety of nucleophiles to form tetrasubstituted adamantanones. Aromatic and heteroaromatic nucleophiles have proven to be successful, and oxygen and nitrogen nucleophiles can provide access to a wide breadth of functionality at the newly formed tertiary position.

One-step synthesis of substituted adamantanones from bicyclo[3.3.1]nonanones

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.