Addition of excess hydrogen peroxide (10 equiv) to a sonicated solution of FeS04:7Hz0 ( 1 equiv) in DMSO containing the N-(o4odoalkyl)indoles 4,5, 11, and 13 effected oxidative radical cyclization to 6,7,14, and 15, respectively. The (o4odoalkyl)pyrroles 21,22,27,38, and 49 underwent analogous cyclization reactions to 23, 24, 28, 39, and 50, respectively. The regiochemistry of these radical cyclization reactions was correctly predicted by FMO calculations in all cases but one. For compound 38, FMO calculations indicated that radical attack should take place at both C-3 and C-5. Only the product of cyclization at C-5, i.e., 39, was observed. The enantiomerically pure bicyclic ketone 42, prepared by the above technique from the iodide 53, was converted into 56 which, on catalytic reductio; (HdRh-Al203), gave a mixture of (-)-monomorine (40) and three of ita diastereomers 56-58 (see, however, Note Added in Proof).The intramolecular addition of a radical to an aromatic nucleus followed by oxidation of the new resonancestabilized radical thus produced back to the aromatic system (oxidative radical cyclization) is a process which has considerable synthetic utility, and several methods have recently been devised to effect such cyclizations. For example, oxidative intramolecular additions to aromatic systems mediated by Mn(III),1*2 Fe(II1),2 Cu(II),3 Ce(IV),2p3 and tri-n-butyltin hydride4ts which proceed with varying degrees of efficiency have been reported. As a long-term goal, we have been interested in devising efficient and inexpensive methods of effecting oxidative radical cyclization to aromatic systems. In addition, we have been investigating the use of simple computational methods as a possible means of predicting the regioselectivity of such reactions (Artis et al., ref 1). This publication describes some of our recent results in the indole and pyrrole areas.Dixon et al.6 showed by EPR spectroscopy that methyl radicals were produced in the reaction of hydroxyl radicals (generated from Ti(II1) and hydrogen peroxide) with DMSO. This reaction (eq 1) proceeds in >90 % yield based on hydroxyl radicals produced and also can be applied to sulfoxides other than DMSO.' Torsell and co-workers* + Contribution no. 881 from the