A concise total synthesis of (+/-)-1-epiaustraline.

[reaction: see text] A concise total synthesis of 1-epiaustraline 3 is described that utilizes a diastereoselective Birch reduction of an electron-deficient pyrrole and a chelation-controlled vinyl Grignard addition to an aldehyde to introduce the C7 stereocenter. The C1 and C2 stereocenters were set through an OsO(4)-catalyzed dihydroxylation.