Stereoselektive Synthese enantiomerenreiner Nupharamin-Alkaloide aus dem Castoreum (Bibergeil)

6533b852fe1ef96bd12aaa8f

RESEARCH PRODUCT

Stereoselektive Synthese enantiomerenreiner Nupharamin-Alkaloide aus dem Castoreum (Bibergeil)

André Fischer Julia Baron Markus Weymann Alexander Stoye Elissavet Kapatsina Gabriele Quandt Björn Brunnhöfer Horst Kunz

subject

General Medicine

description

Tierische Parfumalkaloide: Eine stereoselektive Mannich-Michael-Reaktion an N-Galactosylfurylaldimin zu 1 (Piv = Pivaloyl), anschliesende konjugierte Cuprataddition und stereoselektive Protonierung des gebildeten Enolats, alle kontrolliert vom Kohlenhydrat, ermoglichen erstmals die Totalsynthese des all-cis-Nupharamins 2 aus dem Castoreum. Enolatprotonierung nach Abspaltung des Kohlenhydrats fuhrt alternativ zum Epimer 3.

year	journal	country	edition	language
2009-03-09	Angewandte Chemie

https://doi.org/10.1002/ange.200805606

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