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.
Institut fur Organische Chemie der Universität, Am Hubland, Würzburg, Germany. bringman@chemie.uni-wuerzburg.de
G
G
Bringmann
K
K
Messer
W
W
Saeb
E M
EM
Peters
K
K
Peters
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