Total synthesis of alkaloid (+/-)-G. B. 13 using a Rh(I)-catalyzed ketone hydroarylation and late-stage pyridine reduction.
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.
Larson
Kimberly K
KK
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Sarpong
Richmond
R
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*
D000470:Alkaloids; D004952:Esters; D007659:Ketones; D010880:Piperidines; D011725:Pyridines; C032727:piperidine; D012238:Rhodium; D001895:Boron; C023666:pyridine