The absolute configuration of (+)-isoshinanolone and in situ LC-CD analysis of its stereoisomers from crude extracts.
The absolute configuration of (+)-isoshinanolone, a wide-spread acetogenic metabolite from higher plants, has been determined by X-ray structure analysis of its new dibromide; accordingly, this natural tetralone is 3R,4R-configured, in agreement with previous degradative results. In addition, a first chiroptical on-line stereoanalysis for isoshinanolones is presented, i.a. by HPLC on a chiral phase coupled to CD spectroscopy, giving pure CD spectra of all of the four stereoisomers of isoshinanolone directly from stereoisomeric mixtures.
Bringmann
G
G
Institut fur Organische Chemie der Universität, Am Hubland, Würzburg, Germany. bringman@chemie.uni-wuerzburg.de
Messer
K
K
Saeb
W
W
Peters
E M
EM
Peters
K
K
D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010936:Plant Extracts / Q000737:chemistry; D010944:Plants / Q000737:chemistry*; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000737:chemistry*
D010936:Plant Extracts; D013764:Tetrahydronaphthalenes; C434363:isoshinanolone