Application of a stereospecific RhCl(PPh3)3 decarbonylation reaction for the total synthesis of 7-(±)-deoxypancratistatin

A highly efficient total synthesis of 7-deoxypancratistatin is described. The synthesis features the ready preparation of the phenanthridone skeleton by a Stille-IMDAF cycloaddition cascade. The resulting cycloadduct is converted into a key aldehydic intermediate, which is then induced to undergo a stereospecific decarbonylation reaction using Wilkinson’s catalyst to set the trans B-C ring junction of the target molecule.