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We herein describe sequential radical cyclization of acyclic polyenes having a vinyliodide moiety that can act as both of a radical donor and an acceptor during the same reaction. The regioselectivity is extremely dependent on the substrate structure. Tricyclo(8.4.0.0 2,7 )tetradecene and tricyclo(6.3.0.0 2,6 )undecane were obtained by cascade radical cyclization from the well- designed substrates, 1-iodo-1,5,9,14-tetraene and 1-iodo-1,5,10-triene, in a single operation.

Cascade radical cyclization of polyolefinic vinyl iodides: comparison between 5-exo and 6-endo cyclization of vinyl radicals