6533b857fe1ef96bd12b516e
RESEARCH PRODUCT
Stereoselective Synthesis of Enantiomerically Pure Nupharamine Alkaloids from Castoreum
Markus WeymannHorst KunzAndré FischerJulia BaronAlexander StoyeElissavet KapatsinaBjörn BrunnhöferGabriele Quandtsubject
IndolizidinesIndolizidinesTerpenesChemistryStereochemistryEnantioselective synthesisTotal synthesisRodentiaStereoisomerismProtonationStereoisomerismNupharamineGeneral ChemistryCatalysischemistry.chemical_compoundAlkaloidsPiperidinesAnimalsStereoselectivityEpimerScent GlandsFuransdescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2009-03-09 | Angewandte Chemie International Edition |