Stereoselective synthesis of enantiomerically pure nupharamine alkaloids from castoreum.
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.
Stoye
Alexander
A
Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany.
Quandt
Gabriele
G
Brunnhöfer
Björn
B
Kapatsina
Elissavet
E
Baron
Julia
J
Fischer
André
A
Weymann
Markus
M
Kunz
Horst
H
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D054836:Indolizidines / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D012377:Rodentia; D012543:Scent Glands; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry
D000470:Alkaloids; D005663:Furans; D054836:Indolizidines; D010880:Piperidines; D013729:Terpenes; C520122:nupharamine