BISMURRAYAQUINONE-A - SYNTHESIS, CHROMATOGRAPHIC ENANTIOMER RESOLUTION, AND STEREOANALYSIS BY COMPUTATIONAL AND EXPERIMENTAL CD INVESTIGATIONS

The first total synthesis of a naturally occurring dimeric carbazole alkaloid, bismurrayaquinone A (4), is described, by oxidation of dimeric O-demethylmurrayafoline A, a still hypothetic natural product recently synthesized. By chromatography on a chiral phase, the two atropoenantiomers were separated. The absolute configurations of these two rotational isomers were elucidated by comparison of their calculated spectra with those measured experimentally.