Total Syntheses and Determination of Absolute Configurations of Cep-212 and Cep-210, Predicted Biosynthetic Intermediates of Tetrodotoxin Isolated from Toxic Newt

Masaatsu Adachi, Tadachika Miyasaka, Yuta Kudo, Keita Sugimoto, Mari Yotsu-Yamashita, Toshio Nishikawa

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

Total syntheses of Cep-212 and Cep-210, predicted biosynthetic intermediates of tetrodotoxin isolated from the Japanese toxic newt, have been accomplished from geraniol by an intramolecular hetero Diels-Alder reaction as a key step in a highly stereoselective manner. The success of these syntheses enabled us to determine their absolute configurations by using a chiral normal-phase HPLC/MS analysis of the bis-dinitrobenzene derivative of natural Cep-212 and reference derivatives prepared from chemically synthesized enantiomers. ©

Original languageEnglish
Pages (from-to)780-784
Number of pages5
JournalOrganic letters
Volume21
Issue number3
DOIs
Publication statusPublished - 2019 Feb 1

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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