Abstract Sequential, radical-mediated cyclizations of 1,5-enynes have been evaluated with respect to structure, stereochemistry and reactivity. In series A 5- exo-trig, 6- endo-dig cascades are favoured. The unusual 6- endo-dig cyclization is dictated by ring strain. Diastereomeric series B tolerates leakage into the 5- exo-trig, 5- exo-dig sequence, especially if a quaternary carbon centre is established during the first five-ring cyclization. The cascade allows construction of four and more chiral centres in a single convergent step. The influence of E/ Z geometry of the olefinic component is also evaluated.