title: Toward the total synthesis of Sinefungin.
abstract: Among many attempts toward the total synthesis of Sinefungin one of the most promising approach was found to be the transglycosylation of the amino acid-D-ribofuranosyl portion of 15 to N6-acyladenine. The key intermediate (15) was prepared from uridine in 12 steps. Thus, treatment of 2',3'-O-isopropylidene-uridine 5'-aldehyde (5) with methyl 4-nitrobutanoate gave rise to an aldol adduct (6) which was led to 4-nitro-4-(5'-deoxy-2', 3'-O-isopropylideneuridin-5'-yl)-butanal (10) via 8. A four-component condensation involving 10 afforded N,N-disubstituted alpha-aminocarboxamide derivative (11). The transglycosylation involving 8 and N6-benzoyladenine was successfully achieved. A parallel transglycosylation involving 15 and N6-benzoyladenine is under way to obtain 16.
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000935:Antifungal Agents / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008722:Methods
chemical_list: D000935:Antifungal Agents; D007202:Indicators and Reagents; D000241:Adenosine; C006235:sinefungin