486-88-4Relevant academic research and scientific papers
Simple and highly efficient preparation and characterization of (-)-lupanine and (+)-sparteine
Przyby?, Anna K.,Kubicki, MacIej
experimental part, p. 7787 - 7793 (2011/10/30)
In a simple and convenient way, we have improved the non-chromatographic isolation of optically pure (-)-2-oxosparteine ((-)-lupanine) and (+)-sparteine. The fast and efficient method for the determination of the ee of bisquinolizidine alkaloids has been proposed. A relatively simple simple 1H NMR method has been applied for evaluation of the % ee of enantiomers of the lupanines and sparteines with the chiral dibenzoyltartaric acids as the shift reagents. The 1H NMR spectra of the bases and the new salts in polar solvents have been measured. The results are confirmed by chiral HPLC method. Additionally, for the first time X-ray analysis of the salt of (-)-lupanine has been performed. The improved method of purification of bisquinolizidine alkaloids will considerably facilitate the employment of these alkaloids as chiral ligands in asymmetric reactions and as pharmacological tools.
ABSOLUTE CONFIGURATION OF (+)-5,6-DEHYDROLUPANINE, A KEY INTERMEDIATE IN BIOSYNTHESIS OF LUPIN ALKALOIDS
Saito, Kazuki,Takamatsu, Satoshi,Sekine, Toshikazu,Ikegami, Fumio,Ohmiya, Shigeru,et al.
, p. 958 - 959 (2007/10/02)
(+)-5,6-Dehydrolupanine, a key intermediate in biosynthesis of lupin alkaloids, was isolated from Thermopsis chinensis.The absolute configuration of the compound was determined to be 7R,9R,11R by chemical transformation to (-)-lupanine.Key Word Index - Thermopsis chinensis; Leguminosae; aerial parts; lupin alkaloid; quinolizidine alkaloid; (+)-5,6-dehydrolupanine; lupanine; absolute configuration; biosynthesis.
Synthesis of Cadaverine and its Incorporation into five Quinolizidine Alkaloids
Robins, David J.,Sheldrake, Gary N.
, p. 2101 - 2120 (2007/10/02)
Cadaverine dihydrochloride (13) was synthesised by the sequential introduction of two equivalents of sodium cyanide to a C3 precursor, and it was fed to Lupinus luteus and L. polyphyllus plants.Complete labelling patterns were obtained in five quinolizidine alkaloids by 13C n.m.r. spectroscopy.The 13C-13C doublets observed in the spectra of (-)-lupinine (3), (-)-sparteine (4), (+)-lupanine (5), (+)-13α-hydroxylupanine (6), and (+)-angustifoline (7) derived biosynthetically from the doubly labelled precursor (13) confirm the intact, specific incorporation of two cadaverine units into the tetracyclic quinolizidine alkaloid skeletons.The cadaverine (13) units are incorporated to about the same extent into each part of the quinolizidine alkaloids (3)-(7).Two of the 13C chemical shifts for lupanine (5) have been reassigned.The labelling pattern of the tricyclic alkaloid angustifoline (7) indicates that the allyl group originates by degradation of one ring of a tetracyclic precursor.
Lactams of sparteine
Golebiewski, W. Marek,Spenser, Ian D.
, p. 716 - 719 (2007/10/02)
(2,2-2H2)Sparteine, (6-2H)sparteine, (10,10-2H2)sparteine, (15,15-2H2)sparteine, (17α-2H)sparteine, (17β-2H)sparteine, (17,17-2H2)sparteine, (17α-2H)lupanine, and (17β-2H)lupanine were prepared and employed to assign the 1H nmr spectrum of sparteine.Contrary to a published report, photochemical oxidation of sparteine does not lead to 15-oxosparteine but to 17-oxosparteine.
