Synthesis and determination of the relative structure of akaterpin, a potent inhibitor of PI-PLC

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

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

We describe the first total synthesis and structural determination of akaterpin, an inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC). The key features of the synthetic strategy include a regio- and stereoselective C-alkylation at the angular C1′ position and an exo-selective intermolecular Diels-Alder reaction. The relative stereochemistry was determined by a comparison of the NMR spectra of synthetic akaterpin with those of natural akaterpin.

Original languageEnglish
Pages (from-to)4961-4964
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number38
DOIs
Publication statusPublished - 2011 Sep 21
Externally publishedYes

Keywords

  • Diastereoselective Diels-Alder reaction
  • PI-PLC inhibitor
  • Structure determination
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis and determination of the relative structure of akaterpin, a potent inhibitor of PI-PLC'. Together they form a unique fingerprint.

  • Cite this

    Hosoi, H., Kawai, N., Hagiwara, H., Suzuki, T., Nakazaki, A., Takao, K. I., Umezawa, K., & Kobayashi, S. (2011). Synthesis and determination of the relative structure of akaterpin, a potent inhibitor of PI-PLC. Tetrahedron Letters, 52(38), 4961-4964. https://doi.org/10.1016/j.tetlet.2011.07.079