Enantioselective total synthesis and X-ray structures of the tetrahydroprotoberberine alkaloids (-)-(S)-tetrahydropalmatrubine and (-)-(S)-corytenchine.
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.
Zein
Ahmed L
AL
Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland and Labrador, A1B3X7, Canada.
Dawe
Louise N
LN
Georghiou
Paris E
PE
D001600:Berberine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
C552147:(S)-tetrahydropalmatrubine; D001600:Berberine Alkaloids; C507790:corytenchine