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

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

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)

University of Southampton
Saint-Dizier, Alexandre Christian Claude
Saint-Dizier, Alexandre Christian Claude

Saint-Dizier, Alexandre Christian Claude (2002) Samarium Diiodide medicated cascade radical Cyclisations of Methylenecyclopropane derivatives Synthesis of Bioyclo-(3.2.1.)- Oct. University of Southampton, Doctoral Thesis.

Record type: Thesis (Doctoral)

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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Published date: 2002

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Local EPrints ID: 464592
URI: http://eprints.soton.ac.uk/id/eprint/464592
PURE UUID: 95300cca-0a92-4631-9311-770a78b39911

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Date deposited: 04 Jul 2022 23:49
Last modified: 05 Jul 2022 02:33

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Author: Alexandre Christian Claude Saint-Dizier

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