The cytotoxicity of ent-kauranic derivatives functionalized with azide, lactam and pyrrolidine fragments has been demonstrated. The inverstigated compounds showed relevant activity against Capan-1 (pancreatic adenocarcinoma), Hap-1 (chronic myeloid leukemia), HCT-116 (colorectal carcinoma), NCI-H460 (lung carcinoma), DND-41 (acute lymphoblastic leukemia), HL-60 (acute myeloid leukemia), K-562 (chronic myeloid leukemia), and Z-138 (non-Hodgkin lymphoma) cancer cell lines. The selectivity index was demonstrated by higher IC50 values in normal retina cells (hTERT RPE-1). The ent-kauranic azides 1 and 2 have been synthesized by radical carboazidation reactions using two different methods: first with hexabutylditin as radical transfer reagent and di-tert-butyl hyponitrite (DTBHN) as radical initiator and the second with triethylborane in the presence of air [1, 2]. Compounds 1 and 2 were converted to lactams 3 and 4, the lactam 3 was reduced to pyrrolidine 5. Figure 1 Compounds 1 - 5 presented in Figure 1 are air- and moisture stable, soluble in DMSO and other organic solvents.