Reaction of chiral nucleophiles with pyridinium compounds. Total synthesis of the indole alkaloids (-)-isovallesiachotamine and (+)-vallesiachotamine

Robert Amann, Karen Arnold, Dietrich Spitzner, Zsuzsanna Majer, Günther Snatzke

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13 Citations (Scopus)

Abstract

The addition of the chiral nucleophiles Na-2 and Li-5 to pyridinium compounds 1 and the subsequent ring closure (Pictet-Spengler cyclization) to indoloquinolizines 3a and 7b, respectively, proceed stereoselectively (d.e. for 3a: 54%; for 7b: ≥95 %). Proof for the absolute configuration of these products is provided by their CD spectral data and the transformation of 7b into the indole alkaloids (+)-vallesiachotamine [(Z)-6] and (-)-isovallesiachotamine [(E)-6].

Original languageEnglish
Pages (from-to)349-355
Number of pages7
JournalLiebigs Annales
Issue number3
Publication statusPublished - Mar 1 1996

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Keywords

  • (+)-Vallesiachotamine
  • (-)-Isovallesiachotamine
  • Diastereoselective synthesis
  • Indole alkaloids

ASJC Scopus subject areas

  • Chemistry(all)

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