The remarkable effect of cosolvent on a samarium(II)-mediated 4-exo-trig cyclization: Further synthetic studies on pestalotiopsin A

David J. Edmonds, Kenneth W. Muir, David J. Procter

    Research output: Contribution to journalArticlepeer-review

    Abstract

    A samarium(II)-mediated 4-exo-trig cyclization in which a remote stereocenter serves to control the facial selectivity of the cyclization is described. The apparent coordination of a tertbutyldimethylsilyl ether to the samarium center appears to give rise to the selectivity. The remarkable effect of the cosolvent, 2,2,2-trifluoroethanol, on the cyclization of this substrate, is also discussed. A stereoselective synthesis of the general class of γ,δ-unsaturated aldehyde cyclization substrate is reported, and the utility of the cyclization is demonstrated in an approach to the fully functionalized core of pestalotiopsin A.
    Original languageEnglish
    Pages (from-to)3190-3198
    Number of pages8
    JournalJournal of Organic Chemistry
    Volume68
    Issue number8
    DOIs
    Publication statusPublished - 18 Apr 2003

    Keywords

    • Crystal structure; Molecular structure (of furanone derivs.); Asymmetric synthesis and induction (prepn. and samarium-mediated stereoselective 4-exo-trig cyclization of furanone derivs., effect of trifluoroethanol as cosolvent, and asym. synthesis of pestalotiopsin A core); Cyclization (stereoselective, 4-exo-trig; prepn. and samarium-mediated stereoselective 4-exo-trig cyclization of furanone derivs., effect of trifluoroethanol as cosolvent, and asym. synthesis of pestalotiopsin A core)

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