Determination of the Absolute Structure of (+)-Akaterpin

Hayato Hosoi; Nobuyuki Kawai; Hideki Hagiwara; Takahiro Suzuki; Atsuo Nakazaki; Ken-ichi Takao; Kazuo Umezawa; Susumu Kobayashi

doi:10.1248/cpb.60.137

Regular Articles

Determination of the Absolute Structure of (+)-Akaterpin

Hayato Hosoi, Nobuyuki Kawai, Hideki Hagiwara, Takahiro Suzuki, Atsuo Nakazaki, Ken-ichi Takao, Kazuo Umezawa, Susumu Kobayashi

Author information

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

Keywords: total synthesis, absolute stereochemistry, optical resolution

JOURNAL FREE ACCESS

2012 Volume 60 Issue 1 Pages 137-143

DOI https://doi.org/10.1248/cpb.60.137

Details

Abstract

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.

Corresponding author

Register with J-STAGE for free!