Fluoranthene: Synthesis and Mutagenicity of Four Diol Epoxides

Article abstract of DOI:10.1021/jo00146a011

The syntheses of diol epoxides 4a,b and 5a,b of the mutagenic hydrocarbon fluoranthene (1) are described.Standard methodology is applied to the synthesis of targets 4a,b but fails for the synthesis of 5a,b.The latter two diol epoxides can be assembled by a route utilizing stereoselective, directed epoxidations.Simple molecular orbital calculations have been used to predict the reactivity of the diol epoxides in their opening to triol carbocations.Diol epoxides 4a,b are predicted to be substantially more reactive than isomers 5a,b.The more reactive pair, 4a,b, mayyield carbocations capable of alkylating cellular genetic material.This prediction is borne out in terms of the relative mutagenicity of the diol epoxides in a bacterial screen.