title: Total synthesis of alkaloid (+/-)-G. B. 13 using a Rh(I)-catalyzed ketone hydroarylation and late-stage pyridine reduction.
abstract: Total synthesis of the Galbulimima alkaloid G. B. 13 was achieved utilizing a functionalized pyridine moiety as a piperidine surrogate. Key to the success of the synthesis was the development of an unprecedented rhodium-catalyzed 1,2-addition of an arylboronic ester into an unactivated ketone.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Kimberly K
authors.initials: KK
authors.lastname: Larson
authors.forename: Richmond
authors.initials: R
authors.lastname: Sarpong
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D001895:Boron / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D004952:Esters; D007659:Ketones; D010880:Piperidines; D011725:Pyridines; C032727:piperidine; D012238:Rhodium; D001895:Boron; C023666:pyridine