Asymmetric Total Synthesis of (-)-Clovan-2,9-dione Using Rh(I)-Catalyzed [3 + 2 + 1] Cycloaddition of 1-Yne-vinylcyclopropane and CO.

The asymmetric total synthesis of clovan-2,9-dione with a [6.3.1.01,5]dodecane skeleton has been achieved. The synthesis features a Rh(I)-catalyzed [3 + 2 + 1] cycloaddition of 1-yne-vinylcyclopropane (1-yne-VCP) with CO and an intramolecular aldol reaction to obtain the skeleton of the target molecule.