title: Pd-catalyzed arylation reactions with phenol diazonium salts: application in the synthesis of diarylheptanoids.
abstract: The first total synthesis of the natural product (3S,7R)-5,6-dehydro-de-O-methyl centrolobine and various analogues is reported, using a highly regio- and diastereoselective Mizoroki-Heck reaction of phenol diazonium salts and enantiopure dihydropyrans. The assigned relative configuration was confirmed by single-crystal X-ray structure analysis, but a revision of the absolute configuration is proposed based on polarimetric measurement.
authors: Institut fuer Chemie (Organische Synthesechemie), Universitaet Potsdam, Karl-Liebknecht-Strasse 24-25, D-14476 Potsdam-Golm, Germany. bernd.schmidt@uni-potsdam.de
authors: Bernd
authors: B
authors: Schmidt
authors: Frank
authors: F
authors: Hölter
authors: Alexandra
authors: A
authors: Kelling
authors: Uwe
authors: U
authors: Schilde
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D036381:Diarylheptanoids / Q000138:chemical synthesis* / Q000737:chemistry; D003979:Diazonium Compounds / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D019800:Phenol / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D001688:Biological Products; D036381:Diarylheptanoids; D003979:Diazonium Compounds; D004988:Ethers, Cyclic; D011714:Pyrans; C432457:centrolobin; D019800:Phenol; D010165:Palladium