355022-27-4Relevant academic research and scientific papers
First, atropo-enantioselective total synthesis of the axially chiral phenylanthraquinone natural products knipholone and 6′-O-methylknipholone
Bringmann, Gerhard,Menche, Dirk
, p. 1687 - 1690 (2001)
The first stereoselective access to an axially chiral arylanthraquinone, the antimalarial natural product knipholone (3), was achieved by application of the "lactone concept". Key steps were the intramolecular coupling of the bromoester 1, to give the configurationally unstable biaryl lactone 2, and the enantioselective ring cleavage to form 3.
Atropo-enantioselective total synthesis of knipholone and related antiplasmodial phenylanthraquinones
Bringmann, Gerhard,Menche, Dirk,Kraus, Juergen,Muehlbacher, Joerg,Peters, Karl,Peters, Eva-Maria,Brun, Reto,Bezabih, Merhatibeb,Abegaz, Berhanu M.
, p. 5595 - 5610 (2007/10/03)
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.
