Total Syntheses of rac- and (+)-Goniomitine

Eunjoon Park, Cheol Hong Cheon

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Concise total syntheses of rac- and (+)-goniomitine were developed. The cyanide-catalyzed imino-Stetter reaction of an aldimine, derived from ethyl 2-aminocinnamate and either rac- or (S)-α,β-unsaturated aldehyde bearing a δ-valerolactam at the β-position, provided rac- or (S)-indole-3-acetate carrying an α-vinyl-δ-valerolactam scaffold at the 2-position, respectively. Subsequent saturation of the vinyl group, followed by treatment with DIBAL-H, afforded N-benzyl protected goniomitine. Final debenzylation provided the desired natural product after only three column separations. (Figure presented.).

Original languageEnglish
Pages (from-to)4888-4892
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume361
Issue number21
DOIs
Publication statusPublished - 2019 Nov 5

Keywords

  • Asymmetric synthesis
  • Biomimetic total synthesis
  • Cyanide
  • goniomitine
  • Imino-Stetter reaction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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