A concise synthesis of (+/-)-cylindricine C and its C(13)-epimer is described. Starting from 1-octyne, cylindricine C and 13-epi-cylindricine C were prepared in 11% and 15% yields, respectively. The synthesis involves the preparation of the central tricyclic moiety via a radical alpha-iodoketone carboazidationibis-reductive amination sequence. Inversion of the stereochemistry at C(13) and C(5) was efficiently achieved on late stage intermediates.