Determination of the absolute structure of (+)-akaterpin

Hayato Hosoi, Nobuyuki Kawai, Hideki Hagiwara, Takahiro Suzuki, Atsuo Nakazaki, Ken Ichi Takao, Kazuo Umezaw, Susumu Kobayashi

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2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)137-143
Number of pages7
JournalChemical and Pharmaceutical Bulletin
Volume60
Issue number1
DOIs
Publication statusPublished - 2012 Jan 1
Externally publishedYes

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Keywords

  • Absolute stereochemistry
  • Optical resolution
  • Total synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

Cite this

Hosoi, H., Kawai, N., Hagiwara, H., Suzuki, T., Nakazaki, A., Takao, K. I., Umezaw, K., & Kobayashi, S. (2012). Determination of the absolute structure of (+)-akaterpin. Chemical and Pharmaceutical Bulletin, 60(1), 137-143. https://doi.org/10.1248/cpb.60.137