A facile approach to tricyclo[6.4.0.04,9]-dodecane framework

The unusual tricyclo[6.4.0.04,9]dodecane framework was constructed in eight linear steps in 13% overall yield. An innovative strategy accessing the framework from bicyclo[3.3.1]nonanes was employed. The key steps involve a Robinson annulation, a base induced decarboxylation and epimerization in a single step, and an intramolecular alkylation.

Graphical abstractThe unusual tricyclo[6.4.0.04,9]dodecane framework was constructed in eight linear steps in 13% overall yield. An innovative strategy accessing the framework from bicyclo[3.3.1]nonanes was employed. The key steps involve a Robinson annulation, a base induced decarboxylation and epimerization in a single step, and an intramolecular alkylation. This approach not only provides an access to the tricyclo[6.4.0.04,9]dodecane framework, but also is a potential access to other types of cis-decalin bearing a 1,5-bridging skeleton.Figure optionsDownload full-size imageDownload as PowerPoint slide