Virantmycin antiviral activity

Virantmycin (119) isolated from S. nitrosporeus [103] exhibits an antiviral activity [104] and a weak antifungal activity. It prevents peroxidation of lipids in rat liver microsomes. In the cell assay, benzastatins C and D inhibited glutamate toxicity in N 18-RE-105 cells with EC50 values of 2.0 and 5.4 pM, respectively [105]. Pyrroxamycin (98) isolated from an unidentified streptomycete [106] was found to inhibit Gram-positive bacteria and dermatophytes. 

Virantmycin (233) is a highly unusual metabolite produced by Streptomyces which has been found to possess pronounced antiviral activity. In a total synthesis of (233), described by Hill and... 

The synthetic practicality of the Meyer-Schuster rearrangement was demonstrated in the synthesis of ( )-virantmycin, a metabolite of Streptomyces nitrosporeus, which has been shown to possess antiviral activity. When the attempted conversion of 17 to 19 via a hydrogenation/cyclization sequence was unsuccessful, an alternate pathway utilizing the Meyer-Schuster reaction was explored. Treatment of 17 with acid was presumed to give the a,P-unsaturated ketone which underwent a spontaneous Michael reaction to give 18. Reduction of the resulting ketone 18 was followed by dehydration to provide 19. 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ , ]

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