An Expeditious Synthesis of Lasofoxifene and Nafoxidine via the Novel Three-component Coupling Reaction

  • Yoshiyuki Sano
    Department of Applied Chemistry, Faculty of Science, Tokyo University of Science
  • Kenya Nakata
    Department of Applied Chemistry, Faculty of Science, Tokyo University of Science
  • Takafumi Otoyama
    Department of Applied Chemistry, Faculty of Science, Tokyo University of Science
  • Sei Umeda
    Department of Applied Chemistry, Faculty of Science, Tokyo University of Science
  • Isamu Shiina
    Department of Applied Chemistry, Faculty of Science, Tokyo University of Science

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Abstract

<jats:title>Abstract</jats:title> <jats:p>The simple and efficient synthesis of lasofoxifene (4), a possible candidate for alleviating osteoporosis, via the novel three-component coupling reaction among 4-pivaloyloxybenzaldehyde (5), cinnamyltrimethylsilane (6), and anisole in the presence of HfCl4 is illustrated. The successive cationic cyclization of the coupling product, olefin formation, and migration of the double-bond are performed to afford the common synthetic intermediate of lasofoxifene (4) and nafoxidine (3) via a very concise procedure.</jats:p>

Journal

  • Chemistry Letters

    Chemistry Letters 36 (1), 40-41, 2006-12-02

    Oxford University Press (OUP)

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