Relative and absolute configuration of aloperine.
The relative and absolute configuration of the title compound, (6R,7R,9R,11S)-16,17-didehydro-9-de-2-piperidinylormosanine, C15H24N2, has been elucidated. Two X-ray structures, one of the free base of the alkaloid and the second of its dihydrochloride monohydrate salt, C15H26N2(2+).2Cl-.H2O, have been determined to unequivocally establish the stereochemistry of aloperine, the parent member of a rare family of lupinine alkaloids.
Brosius
A D
AD
Department of Chemistry, University of California, Irvine 92697-2025, USA. abrosius@uci.edu
Ziller
J W
JW
Zhang
Q
Q
D000470:Alkaloids / Q000737:chemistry*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry*; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D010880:Piperidines; D054837:Quinolizidines; D013237:Stereoisomerism
D000470:Alkaloids; D000894:Anti-Inflammatory Agents, Non-Steroidal; D010880:Piperidines; D054837:Quinolizidines; C062701:aloperine