Synthesis of pteroenone and its stereoisomers, a defensive metabolite of the abducted antarctic pteropod clione antarctica

Hiroki Asao, Yoko Nakamura, Yukito Furuya, Shigefumi Kuwahara, Bill J. Baker, Hiromasa Kiyota

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Four stereoisomers of (+)-pteroenone, a defensive metabolite of the abducted Antarctic pteropod Clione antarctica, were synthesized by employing anti-/syn-selective aldol reactions as the key step. These compounds displayed no antifeedant activity against a generally benthic Antarctic fish that does not co-occur with this pteropod.

Original languageEnglish
Pages (from-to)1933-1944
Number of pages12
JournalHelvetica Chimica Acta
Volume93
Issue number10
DOIs
Publication statusPublished - Oct 1 2010
Externally publishedYes

Keywords

  • Aldol reaction
  • Clione antarctica
  • Marine natural products
  • Metabolites
  • Pteroenone

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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