title: Stereoselective synthesis of enantiomerically pure nupharamine alkaloids from castoreum.
abstract: 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.
authors.affiliation: Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany.
authors.forename: Alexander
authors.initials: A
authors.lastname: Stoye
authors.forename: Gabriele
authors.initials: G
authors.lastname: Quandt
authors.forename: Björn
authors.initials: B
authors.lastname: Brunnhöfer
authors.forename: Elissavet
authors.initials: E
authors.lastname: Kapatsina
authors.forename: Julia
authors.initials: J
authors.lastname: Baron
authors.forename: André
authors.initials: A
authors.lastname: Fischer
authors.forename: Markus
authors.initials: M
authors.lastname: Weymann
authors.forename: Horst
authors.initials: H
authors.lastname: Kunz
mesh_terms: 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
chemical_list: D000470:Alkaloids; D005663:Furans; D054836:Indolizidines; D010880:Piperidines; D013729:Terpenes; C520122:nupharamine