Synthesis, stereostructure, and conformations of novel Bi- and trifunctional (+)-isomenthone derivatives

John M. Gardiner, Philip D. Crewe, Gillian E. Smith, Kenneth T. Veal, Robin G. Pritchard, John E. Warren

    Research output: Contribution to journalArticlepeer-review

    Abstract

    (Matrix presented) Following protection, keto alcohols 4 [from (+)-isomenthone] undergo reduction to 1,3-diol 6 (S configuration at the new stereocenter). Organometallic C-nucleophiles add to the carbonyl with the same facial selectivity as hydride, providing multifunctional derivatives, e.g., 8 and 9, with five contiguous stereocenters. The side chain hydroxyl of 4 is elaborated into amino and amide derivatives (e.g., 12). Structural analysis shows that 6, 8, 9, and the precursor to 12 (10) all adopt triaxial solid-state conformations.
    Original languageEnglish
    Pages (from-to)467-470
    Number of pages3
    JournalOrganic Letters
    Volume5
    Issue number4
    DOIs
    Publication statusPublished - 20 Feb 2003

    Keywords

    • Molecular structure (of isopropylmethylcyclohexanol deriv.); Conformation (prepn., stereostructure, and conformations of bi- and trifunctional (+)-isomenthone derivs.)

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