Premium
Stereoselective Synthesis of Enantiomerically Pure Nupharamine Alkaloids from Castoreum
Author(s) -
Stoye Alexander,
Quandt Gabriele,
Brunnhöfer Björn,
Kapatsina Elissavet,
Baron Julia,
Fischer André,
Weymann Markus,
Kunz Horst
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200805606
Subject(s) - stereoselectivity , chemistry , stereochemistry , organic chemistry , catalysis
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 .