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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
 
 
 
 

Selective deoxygenation and O-methylation of benanomicin A: synthesis of 9-deoxy-, 9-O-methyl- and 14-O-methylbenanomicin A.

The selective modifications of phenolic hydroxy groups in the chromophore of benanomicin A are described. Hydride reduction of 9-O-tosylate with sodium borohydride/nickel chloride led to 9-deoxybenanomicin A. Methylation of 1-O-diphenylmethylbenanomicin A diphenylmethyl ester with sodium hydride/iodomethane gave 9-O-methyl derivative and with Hünig's base/diazotrimethylsilylmethane afforded the 14-O-methyl derivative. These compounds showed the diminished activity against fungi.[1]

References

  1. Selective deoxygenation and O-methylation of benanomicin A: synthesis of 9-deoxy-, 9-O-methyl- and 14-O-methylbenanomicin A. Nishizuka, T., Hirosawa, S., Hamada, M., Kondo, S., Ikeda, D., Takeuchi, T. J. Antibiot. (1997) [Pubmed]
 
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