0000000000924116

AUTHOR

Julia Baron

showing 2 related works from this author

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

2009

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.

General MedicineAngewandte Chemie
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Stereoselective Synthesis of Enantiomerically Pure Nupharamine Alkaloids from Castoreum

2009

An animalic note: The first total synthesis of the all-cis nupharamine 2, an alkaloid from beaver castoreum, is based on the stereoselective domino Mannich-Michael reaction of N-galactosylfurylaldimine to give 1 (Piv = pivaloyl), subsequent conjugate cuprate addition, and stereoselective protonation of the enolate. These reactions are all controlled by the carbohydrate. Protonation of the enolate after cleavage of the auxiliary leads to epimer 3.

IndolizidinesIndolizidinesTerpenesChemistryStereochemistryEnantioselective synthesisTotal synthesisRodentiaStereoisomerismProtonationStereoisomerismNupharamineGeneral ChemistryCatalysischemistry.chemical_compoundAlkaloidsPiperidinesAnimalsStereoselectivityEpimerScent GlandsFuransAngewandte Chemie International Edition
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