The synthetically challenging and highly functionalized azabicyclo[6.4.1] ring system, which is found in lycopodium alkaloid lycoclavatumide and some natural molecules, was synthesized for the first time. The key reaction was a diastereoselective type II [5+2] cycloaddition with excellent functional group compatibility. We tried to install the desired eight-membered ring in the final product by RCM reaction.