Reaction of Chiral Nucleophiles with Pyridinium Compounds. Total Synthesis of the Indole Alkaloids (−)-Isovallesiachotamine and (+)-Vallesiachotamine

Autor:	Dietrich Spitzner, Günther Snatzke, Karen Arnold, Zsuzsanna Majer, Robert Amann
Rok vydání:	2006
Předmět:	Indole test Nucleophile Pyridinium Compounds Chemistry Organic Chemistry Absolute configuration Total synthesis Vallesiachotamine General Chemistry Physical and Theoretical Chemistry Spectral data Ring (chemistry) Medicinal chemistry
Zdroj:	Liebigs Annalen. 1996:349-355
ISSN:	1099-0690 0947-3440
DOI:	10.1002/jlac.199619960309
Popis:	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].
Databáze:	OpenAIRE
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