The enantioselective synthesis of (+)-isolysergol was completed in 18 steps, and an overall yield of 11% was obtained from (2R)-(+)-phenyloxirane as a chiral pool. Key features of the synthesis include a stereoselective intramolecular 1,3-dipolar addition of nitrone with terminal olefin and a Cope elimination to furnish the D ring. A rhodium-catalyzed intramolecular [3 + 2] annulation of a benzene ring with α-imino carbenoid was designed to afford the 3,4-fused indole scaffold at the late stage of the synthesis.