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

Robert Amann, Karen Arnold, Dietrich Spitzner, Zs. Majer, Günther Snatzke

Research output: Contribution to journalArticle

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 1996

Fingerprint

Pyridinium Compounds
Indole Alkaloids
Nucleophiles
Cyclization
vallesiachotamine

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Reaction of chiral nucleophiles with pyridinium compounds. Total synthesis of the indole alkaloids (-)-isovallesiachotamine and (+)-vallesiachotamine. / Amann, Robert; Arnold, Karen; Spitzner, Dietrich; Majer, Zs.; Snatzke, Günther.

In: Liebigs Annales, No. 3, 03.1996, p. 349-355.

Research output: Contribution to journalArticle

@article{c92c8586782b4778b27fc2a410c8490a,
title = "Reaction of chiral nucleophiles with pyridinium compounds. Total synthesis of the indole alkaloids (-)-isovallesiachotamine and (+)-vallesiachotamine",
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].",
keywords = "(+)-Vallesiachotamine, (-)-Isovallesiachotamine, Diastereoselective synthesis, Indole alkaloids",
author = "Robert Amann and Karen Arnold and Dietrich Spitzner and Zs. Majer and G{\"u}nther Snatzke",
year = "1996",
month = "3",
language = "English",
pages = "349--355",
journal = "Annalen der Pharmacie",
issn = "0365-5490",
publisher = "Wiley-VCH Verlag",
number = "3",

}

TY - JOUR

T1 - Reaction of chiral nucleophiles with pyridinium compounds. Total synthesis of the indole alkaloids (-)-isovallesiachotamine and (+)-vallesiachotamine

AU - Amann, Robert

AU - Arnold, Karen

AU - Spitzner, Dietrich

AU - Majer, Zs.

AU - Snatzke, Günther

PY - 1996/3

Y1 - 1996/3

N2 - 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].

AB - 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].

KW - (+)-Vallesiachotamine

KW - (-)-Isovallesiachotamine

KW - Diastereoselective synthesis

KW - Indole alkaloids

UR - http://www.scopus.com/inward/record.url?scp=33748909888&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33748909888&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:33748909888

SP - 349

EP - 355

JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0365-5490

IS - 3

ER -