Samarium Diiodide medicated cascade radical Cyclisations of Methylenecyclopropane derivatives Synthesis of Bioyclo-(3.2.1.)- Oct

Abstract

Chapter 2 describes the nucleophilic addition of lithiated methylenecyclopropane to epoxides and studies towards synthesis of keto-alcohol derivatives of methylenecyclopropane such as 189. (Fig. 3929A)

Chapter 3 details the of samarium diiodide mediated cascade cyclisation of methylenecyclopropyl methyl ketones 285 and 327. Bicyclic compounds 305 and 348 were obtained in reasonable to good yields and good diastereoselectivity. The cyclisations of these precursors were found to be stereoselective due to chelation control with the samarium (III) species. (Fig. 3929B)

Chapter 4 concentrates on the synthesis of phenyl ketone derivatives of methylenecyclopropane 351 and 352 and their cyclisation, which failed to give bicyclo-octanes 353 and 354. (Fig. 3929C)

Chapter 5 presents the synthesis and samarium diiodide mediated radical cyclisations of cyclic ketone derivatives of methylenecyclopropane 400 towards tricyclic compounds 401. (Fig. 3929D)

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