The first 6′-O-sulfated phenylanthraquinones: isolation from Bulbine frutescens, structural elucidation, enantiomeric purity, and partial synthesis

Autor: Reto Brun, Gerhard Bringmann, Joan Mutanyatta, Berhanu M. Abegaz, Merhatibeb Bezabih, Michael Dreyer, Nikolaus Kocher
Rok vydání: 2005
Předmět:
Zdroj: Tetrahedron. 61:8475-8484
ISSN: 0040-4020
DOI: 10.1016/j.tet.2005.06.055
Popis: From the roots of Bulbine frutescens, the first sulfated phenylanthraquinones were isolated, together with their known sulfate-free analogs. Their structures were elucidated by spectroscopic and chiroptical methods, by acid hydrolysis or by partial synthesis. The new compounds have the usual stereo-orientation at the biaryl axis (i.e., with the acetyl portion above the anthraquinone plane) except for sodium ent-knipholone 6′-O-sulfate (and thus, also its hydrolysis product, ent-knipholone), which exhibit an opposite axial configuration. We also describe the first stereoanalysis of natural phenylanthraquinones, some of which were found to be not enantiomerically pure, some even near-racemic. We furthermore, report on the first X-ray structure analysis of a phenylanthraquinone, viz. 4′-O-demethylknipholone.
Databáze: OpenAIRE