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Concise Synthesis of Acetal-Protected syn 1,3-Diols by a Tandem Hemiacetal Formation/Tsuji–Trost Reaction

Authors

  • Dr. Liang Wang,

    1. Universität Heidelberg, Organisch-Chemisches Institut, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany)
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  • Prof. Dr. Dirk Menche

    Corresponding author
    1. Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany)
    • Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany)
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  • We thank the Deutsche Forschungsgemeinschaft (SFB 623 “Molekulare Katalysatoren: Struktur und Funktionsdesign”) and the Wild-Stiftung for financial support.

Abstract

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Designed, developed, and applied: A novel domino sequence was used for the rapid assembly of acetal-protected syn 1,3-diols. The convergent synthesis of a polyol fragment of the macrolide antibiotic RK-397 demonstrates that this method is suitable for the rapid and stereoselective preparation of polyketide-type diol motifs.

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