Short total synthesis of 8,10-di-O-methylbergenin.
[reaction: see text] A short, high-yielding synthesis of the C-glucoside 8,10-di-O-methylbergenin is reported. Key elements of the synthesis are a stereoselective installation of a beta-C-aryl linkage, a palladium(0)-catalyzed aryl carbonylation, and a regioselective lactonization reaction. This pathway should allow access to a host of bergenin analogues.
Herzner
Holger
H
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Palmacci
Emma R
ER
Seeberger
Peter H
PH
D000998:Antiviral Agents / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis*; D006027:Glycosides; D007783:Lactones / Q000737:chemistry; D009005:Monosaccharides / Q000138:chemical synthesis; D010165:Palladium / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry
C476088:8,10-di-O-methylbergenin; D000998:Antiviral Agents; D001578:Benzopyrans; C438934:C-glycoside; D006027:Glycosides; D007783:Lactones; D009005:Monosaccharides; D010165:Palladium; C006741:bergenin