Atropo-enantioselective total synthesis of knipholone and related antiplasmodial phenylanthraquinones.
The "lactone concept" has been efficiently employed for the first atropo-enantioselective synthesis of knipholone and related natural phenylanthraquinones. Besides the regio- and stereoselective construction of the biaryl axis, another important step was the "synthetically late" introduction of the C-acetyl group, either by a Friedel-Crafts type acetylation or by an ortho-selective Fries rearrangement first tested on simplified model systems and subsequently applied to the highly atroposelective preparation of the natural products and of simplified analogs thereof for biotesting. The synthetic availability of these natural biaryls, their precursors, and their unnatural analogs permitted a broader investigation of the antiplasmodial activities of these interesting biaryls.
Bringmann
Gerhard
G
Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany. bringman@chemie.uni-wuerzburg.de
Menche
Dirk
D
Kraus
Jürgen
J
Mühlbacher
Jörg
J
Peters
Karl
K
Peters
Eva-Maria
EM
Brun
Reto
R
Bezabih
Merhatibeb
M
Abegaz
Berhanu M
BM
D000107:Acetylation; D000818:Animals; D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D007893:Leishmania donovani / Q000187:drug effects*; D017737:Macrophages, Peritoneal / Q000469:parasitology; D051379:Mice; D008958:Models, Molecular; D008968:Molecular Conformation; D010636:Phenols; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000880:Anthraquinones; D000981:Antiprotozoal Agents; D010636:Phenols