49620-13-5Relevant academic research and scientific papers
Total synthesis of robustaflavone, a potential anti-hepatitis B agent
Zembower, David E.,Zhang, Heping
, p. 9300 - 9305 (2007/10/03)
Robustaflavone, a naturally occurring compound, is an inhibitor of hepatitis B virus replication in vitro. Robustaflavone is a biflavanoid composed of two units of apigenin (5,7,4'-trihydroxyflavone) joined via a biaryl linkage between the 6-position of one unit and the 3'-position of the other (I6,II3'-biapigenin). The natural material was isolated from the seed- kernels of Rhus succedanea. To provide ready access to sufficient quantities of material for continued biological studies, as well as to provide a general route for the preparation of structural analogues, a total synthesis of robustaflavone was pursued. The total synthesis was approached by constructing apigenin ethers containing functionalities at the 6- and 3'- positions which could be cross-coupled using transition metal catalysis. Key steps of the synthesis included development of a regioselective iodination of an apigenin derivative at the 6-position. Also key was the formation of an apigenin 3'-boronate using a palladium-catalyzed exchange of the corresponding 3'-iodide with a diboron reagent. Finally, identification of appropriate reaction conditions for Suzuki coupling to form the sterically congested 6-3''' biaryl bond of robustaflavone provided access to the desired biflavanoid system. This work represents the first total synthesis of robustaflavone.
13C NMR STUDIES OF SOME NATURALLY OCCURRING AMENTOFLAVONE AND HINOKIFLAVONE BIFLAVONOIDS
Markham, Kenneth R.,Sheppard, Carolyn,Geiger, Hans
, p. 3335 - 3338 (2007/10/02)
The 13C NMR spectra of a range of amentoflavone and honokiflavone biflavonoids are reported, most for the first time.Substituent shifts relating to the interflavonoid linkages and to specific methylation patterns are defined and appear to be of diagnostic value.Key Word Index - 13C NMR; amentoflavones; hinokiflavones; methyl ethers; dihydro-derivatives.
