Synthesis of neoechinulin A and derivatives

Kouji Kuramochi, Toshiaki Aoki, Atsuo Nakazaki, Shinji Kamisuki, Masahiro Takeno, Kensuke Ohnishi, Kuniaki Kimoto, Nobuo Watanabe, Takashi Kamakura, Takao Arai, Fumio Sugawara, Susumu Kobayashi

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Neoechinulin A isolated from Eurotium rubrum showed cytoprotection activity against peroxynitrite generated from SIN-1 [3-(4-morpholinyl)sydnonimine hydrochloride] in PC12 cells. As we are interested in this biological activity, we synthesized neoechinulin A and its derivatives. In this article, we fully report the isolation of natural neoechinulin A and B, a total synthesis of (-)-neoechinulin A, and determination of the absolute configuration of natural neoechinulin A. In addition, we describe herein syntheses of neoechinulin A derivatives, including a biotinylated neoechinulin A derivative, which will be useful for identification of the binding proteins of neoechinulin A.

Original languageEnglish
Article numberF15208SS
Pages (from-to)3810-3818
Number of pages9
JournalSynthesis
Issue number23
DOIs
Publication statusPublished - 2008 Dec 1

Keywords

  • Alkaloids
  • Amino acids
  • Antibiotics
  • Indoles
  • Natural products

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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