ABSTRACT
The synthesis of the diterpene (+)-tonantzitlolone A and a series of derivatives is reported. The study includes the determination of their antiproliferative activities against selected cancer cell lines.
Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Diterpenes/chemical synthesis , Diterpenes/pharmacology , Macrocyclic Compounds/chemical synthesis , Macrocyclic Compounds/pharmacology , Antineoplastic Agents/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Chemistry Techniques, Synthetic , Diterpenes/chemistry , Humans , Macrocyclic Compounds/chemistryABSTRACT
The preparation of phenylsulfonate-tagged iodine(III) reagents as well as their use in a novel purification strategy for iodine(III)-promoted reactions is described. The concept is based on ion exchange and is initiated by an azide-promoted SN2-reaction at the alkyl sulfonate followed by trapping of the resulting aryl sulfonate anion with an ion-exchange resin. The concept is successfully proven for Ru-catalyzed oxidations of alcohols, the activation and glycosidation of thioglycosides, and the SuArez reaction of pyranoses.
Subject(s)
Iodine Compounds/chemistry , Iodine Compounds/isolation & purification , Acetonitriles/chemistry , Alcohols/chemistry , Alkanesulfonates/chemistry , Glycosides/chemistry , Ion Exchange , Magnetic Resonance Spectroscopy , Molecular Structure , Oxidation-ReductionABSTRACT
The preparation of the 4-i-butylsulfonate derivative of the Zefirov reagent (5) and its use in a novel purification strategy for iodine(III)-promoted glycosidations of 2-deoxy diethyldithiophosphate glycosides is described.