Free-radical cyclizations: application to the total synthesis of dl-pleurotin and dl-dihydropleurotin acid

Total syntheses of the antitumor antibiotic pleurotin (1) and dihydropleurotin acid (2) are described. Early stages of the synthesis feature the construction of a trans perhydroindan substructure using a stereoselective free-radical cyclization, and the final stage of the synthesis involves the biomimetic conversion of dihydropleurotin acid (2) to pleurotin (1)