Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones

Robin G. Pritchard, Helen M. Sheldrake, Isobel Z. Taylor, Timothy W. Wallace

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    Abstract

    The tetracyclic nucleus of puupehenone, 15-oxopuupehenol and other sesquiterpene-phenol natural products can be assembled stereoselectively in three steps, the last of these being the 6-endo-trig cyclisation of an alpha-keto radical generated from a substituted 2-(2-cyclohexenyl)ethyl 3-bromo-4-chromanone under metal-free conditions. © 2008 Elsevier Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)4156-4159
    Number of pages3
    JournalTetrahedron Letters
    Volume49
    Issue number26
    DOIs
    Publication statusPublished - 23 Jun 2008

    Keywords

    • α-Bromoketone
    • 6-endo-Trig
    • Benzo[a]xanthene
    • Lauroyl peroxide
    • Merosesquiterpene
    • Puupehenone
    • Radical cyclisation
    • Sesquiterpene-phenol

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