Total syntheses of codonopsinine and 4-epi-codonopsinine via gold-mediated tandem-catalyzed pyrrole synthesis

Minami Yamaguchi, Daichi Itagaki, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The total syntheses of codonopsinine (1) and 4-epi-codonopsinine (2) were accomplished. The key substituted pyrrole intermediate was constructed via gold-catalyzed addition-cyclization cascade of an aminoacetaldehyde acetal derivative and a terminal alkyne. After diastereoselective reduction of the pyrrole intermediate to the corresponding 3-pyrroline derivative with zinc dust and sulfonic acid, the total synthesis of 4-epi-codonopsinine (2) was achieved via stereoselective construction of the diol by dihydroxylation. In addition, the total synthesis of codonopsinine (1) was completed through stereochemical inversion of the hydroxyl group via epoxide and subsequent ring cleavage under the acidic aqueous condition.

Original languageEnglish
Pages (from-to)253-258
Number of pages6
JournalJournal of Antibiotics
Volume69
Issue number4
DOIs
Publication statusPublished - 2016 Apr 1

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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