Intramolecular Addition of a Dioxolanyl Radical to the Indole Nucleus: Preparation of Enantiomerically Pure, Oxygenated Perhydro-3H-pyrroloindoles

Article abstract of DOI:10.1021/jo00062a019

The cyclization of dioxolanyl radicals, which were generated by the Barton tartrate-derived thiohydroxamate ester (mixed anhydride) procedure, with an indole nucleus has been explored.The products derived from these reactions have been identified and their chemistry investigated with the goal of uncovering new entries into enantiomerically pure, mitomycin-like structures.Thus, the photolysis of 1-hydroxy-2-thiopyridone ester 8c and 1-hydroxy-4-methylthiazole-2(3H)-thione ester 8d has been conducted with UV and visible light.The photochemistry of the products, namely, dimer 9, dihydroindole 12a, indole 11, and thiazole 13c, derived from the thiohydroxamate esters and putative intermediates 18a and 18b, was also explored.