posted on 2024-01-23, 01:03authored byChuyi Su, Madeleine A. Dallaston, Renée D. Watson, Tyler Fahrenhorst-Jones, Jacob P. Cameron, Gregory K. Pierens, Paul V. Bernhardt, G. Paul Savage, Craig M. Williams
The first synthesis of the 5-aza[1.0]triblattane
skeleton was achieved
through a [4 + 2] cycloaddition approach using a suitably protected
azetine and cyclopentadiene. A series of azetines were synthesized
to explore both stability and suitable N-protection. The key step
following cycloaddition utilized a noninitiated protonated aminyl
radical cyclization to install the final 5-azatriblattane bond, but
it was found to be considerably more unstable than the 6-aza isomer
under acidic conditions.