Determination of the Absolute Structure of (+)-Akaterpin

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  • Hosoi Hayato
    Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI)
  • Kawai Nobuyuki
    Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI)
  • Hagiwara Hideki
    Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI)
  • Suzuki Takahiro
    Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI)
  • Nakazaki Atsuo
    Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI)
  • Takao Ken-ichi
    Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI)
  • Umezawa Kazuo
    Department of Applied Chemistry, Faculty of Science and Technology, Keio University
  • Kobayashi Susumu
    Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI)

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We describe the total synthesis and structural determination of (+)-akaterpin (1), an inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC). The key features of the synthetic strategy include the resolution of β,γ-unsaturated ketone (±)-2a with chiral sulfoximine 6. The absolute stereochemistry was determined by comparison of the specific optical rotation data of (+)-1 and (−)-1 with that of natural akaterpin.

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