Synthesis of a Key Intermediate for the Preparation of FTY720 Analogs

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  • Hamada Maiko
    School of Pharmaceutical Science, Toho University Medicinal Chemistry Research Laboratories I, Research Division, Mitsubishi Tanabe Pharma Corporation
  • Adachi Kunitomo
    Medicinal Chemistry Research Laboratories I, Research Division, Mitsubishi Tanabe Pharma Corporation
  • Hikawa Hidemasa
    School of Pharmaceutical Science, Toho University
  • Yokoyama Yuusaku
    School of Pharmaceutical Science, Toho University

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A concise synthesis of a useful intermediate 10 for the preparation of fingolimod (FTY-720) analogs was achieved by utilizing a chemoselective Sonogashira reaction of trihalobenzene 12 with alkyne 13. The reaction proceeded with high selectivity to give alkyne 11 containing the dihalobenzene moiety in good yield. Compound 11 was converted into intermediate 10 by hydrogenation without reduction of the halogen atoms.

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