Total Synthesis of Two Possible Diastereomers of Natural 6-Chlorotetrahydrofuran Acetogenin and Its Stereostructural Elucidation

Hiroyoshi Takamura, Tomoya Katsube, Kazuki Okamoto, Isao Kadota

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The first total synthesis of two possible diastereomers of natural 6-chlorotetrahydrofuran acetogenin 1 has been achieved. The synthetic route features 5-exo-tet cyclization, Z selective Wittig reaction and Julia olefination for the construction of conjugated diene and enyne moieties, and stereoselective chlorination. Comparison of their 1H and 13C NMR data and specific rotation with those of the natural product elucidated the absolute configuration of natural (−)-6-chlorotetrahydrofuran acetogenin 1.

Original languageEnglish
Pages (from-to)17191-17194
Number of pages4
JournalChemistry - A European Journal
Volume23
Issue number68
DOIs
Publication statusPublished - Dec 6 2017

Keywords

  • natural products
  • stereoselective synthesis
  • structure elucidation
  • tetrahydrofuran
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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