We have accomplished the asymmetric total synthesis of arcutinidine, arcutinine, and arcutine, three arcutine-type C20-diterpenoid alkaloids. A pentacyclic intermediate was rapidly assembled by using two Diels-Alder reactions. We developed a cascade sequence of Prins cyclization and Wagner-Meerwein rearrangement to construct the core of arcutinidine, which was then elaborated into an oxygenated pentacycle through a scalable route. Chemoselective reductive amination followed by spontaneous imine formation furnished the pyrroline motif in the final stage. We clarified the S configuration of the alpha-carbon of the acyl group within arcutine through chemical synthesis and crystallographic analysis.