Fluoranthene: synthesis and mutagenicity of four diol epoxides

…, RB Nachbar Jr, S Russo-Rodriguez…

Index: Rastetter, William H.; Nachbar, Robert B.; Russo-Rodriguez, Sandra; Wattley, Ruth V.; Thilly, William G.; et al. Journal of Organic Chemistry, 1982 , vol. 47, # 25 p. 4873 - 4878

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Citation Number: 46

Abstract

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 ...