Abstract: The readily synthesized enediynes 12a-j possessing a tethered olefin radical acceptor can participate in a tandem enediyneradical cyclization to yield dihydrobenzindene derivatives 14a-j. In the present study, the scope of this reaction was expanded to include a wide variety of olefin acceptors. Substitution at both ends of olefin leads to the formation of two diastereomers 14b and 14c in a 3 3 1 ratio when Rj is Me and R1 is C02Me. The ...