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, Kenichi 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

Fingerprint

Phosphoinositide Phospholipase C
Stereochemistry
Alkylation
Cycloaddition Reaction
Nuclear magnetic resonance
akaterpin

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and determination of the relative structure of akaterpin, a potent inhibitor of PI-PLC. / Hosoi, Hayato; Kawai, Nobuyuki; Hagiwara, Hideki; Suzuki, Takahiro; Nakazaki, Atsuo; Takao, Kenichi; Umezawa, Kazuo; Kobayashi, Susumu.

In: Tetrahedron Letters, Vol. 52, No. 38, 21.09.2011, p. 4961-4964.

Research output: Contribution to journalArticle

Hosoi, H, Kawai, N, Hagiwara, H, Suzuki, T, Nakazaki, A, Takao, K, Umezawa, K & Kobayashi, S 2011, 'Synthesis and determination of the relative structure of akaterpin, a potent inhibitor of PI-PLC', Tetrahedron Letters, vol. 52, no. 38, pp. 4961-4964. https://doi.org/10.1016/j.tetlet.2011.07.079
Hosoi, Hayato ; Kawai, Nobuyuki ; Hagiwara, Hideki ; Suzuki, Takahiro ; Nakazaki, Atsuo ; Takao, Kenichi ; Umezawa, Kazuo ; Kobayashi, Susumu. / Synthesis and determination of the relative structure of akaterpin, a potent inhibitor of PI-PLC. In: Tetrahedron Letters. 2011 ; Vol. 52, No. 38. pp. 4961-4964.
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