A stereoselective cyclisation cascade mediated by SmI2-H 2O: Synthetic studies towards stolonidiol

Thomas M. Baker, Lisa A. Sloan, Lokman H. Choudhury, Masahito Murai, David J. Procter

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    Abstract

    A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemoselective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol. © 2010 Elsevier Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)1246-1261
    Number of pages15
    JournalTetrahedron Asymmetry
    Volume21
    Issue number9-10
    DOIs
    Publication statusPublished - 17 May 2010

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