Total synthesis of chiriquitoxin, an analogue of tetrodotoxin isolated from the skin of a dart frog

Masaatsu Adachi, Takuya Imazu, Ryo Sakakibara, Yoshiki Satake, Minoru Isobe, Toshio Nishikawa

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The first total synthesis of chiriquitoxin, the most structurally complex analogue of tetrodotoxin isolated from a Costa Rican dart frog, has been accomplished from a newly designed intermediate for a variety of tetrodotoxin derivatives. The synthesis includes the third total synthesis of tetrodotoxin in this laboratory, and its intermediate was transformed into chiriquitoxin by a stereocontrolled aldol reaction with a d-camphor-derived lactone for installation of the unique side chain, and a new deprotection of methylthiomethyl (MTM) ether by using a Pummerer rearrangement.

Original languageEnglish
Pages (from-to)1247-1251
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number5
DOIs
Publication statusPublished - 2014 Jan 27
Externally publishedYes

Keywords

  • Chiriquitoxin
  • Natural products
  • Pummerer rearrangement
  • Tetrodotoxin
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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