title: Enantioselective total synthesis and X-ray structures of the tetrahydroprotoberberine alkaloids (-)-(S)-tetrahydropalmatrubine and (-)-(S)-corytenchine.
abstract: Enantioselective total syntheses and X-ray structures of both (S)-tetrahydropalmatrubine (2) and (S)-corytenchine (3) are reported for the first time. They were both derived from (S)-N-norlaudanidine, a benzyltetrahydroisoquinoline that was synthesized with high (>95% ee) enantioselectivity using a chiral auxiliary-assisted Bischler-Napieralski cyclization/reduction approach.
authors.affiliation: Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland and Labrador, A1B3X7, Canada.
authors.forename: Ahmed L
authors.initials: AL
authors.lastname: Zein
authors.forename: Louise N
authors.initials: LN
authors.lastname: Dawe
authors.forename: Paris E
authors.initials: PE
authors.lastname: Georghiou
mesh_terms: D001600:Berberine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C552147:(S)-tetrahydropalmatrubine; D001600:Berberine Alkaloids; C507790:corytenchine