Extending Pummerer reaction chemistry. Synthesis of (+/-)-dibromophakellstatin by oxidative cyclization of an imidazole derivative.
The diastereoselective oxidative cyclization of a dihydrooroidin derivative is reported. The thioimidate product formed by application of a new variant of the Pummerer reaction serves as a precursor to dibromophakellstatin. [reaction: see text]
Feldman
Ken S
KS
Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA. ksf@chem.psu.edu
Skoumbourdis
Amanda P
AP
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000470:Alkaloids; D007093:Imidazoles; D007202:Indicators and Reagents; C104805:dibromophakellstatin