Studies toward synthesis of mono-glycosylated dipyrromethanes and analogues of the anti-cancer natural product tolyporphin

Sammanfattning: The tolyporphin A structure contains a tetrapyrrolic bacteriochlorin macrocycle and also consists of two glycosyl groups directly connected to the pyrroles. In this thesis, 3-glycosylated pyrrole was reacted with Eschenmoser's salt to produce N,N-dimethylamino methylated derivative in 95 % yield. Then, the product was reacted with pyrrole under microwave irradiation to produce glycosylated dipyrromethane in 44 % yield. Mono-glycosylated porphyrin was formed by reacting glycosylated dipyrromethane with 1,9-bis (imino)-5-phenyl dipyrromethane under the standard procedure, 1H NMR was used to confirm the new products.