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.
Nishizuka
T
T
Institute of Microbial Chemistry, M. C. R. F., Tokyo, Japan.
Hirosawa
S
S
Hamada
M
M
Kondo
S
S
Ikeda
D
D
Takeuchi
T
T
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008745:Methylation; D013329:Structure-Activity Relationship; D000095643:Pradimicins and Benanomicins
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D000935:Antifungal Agents; C109010:14-O-methylbenanomicin A; C109009:9-O-methylbenanomicin A; C109008:9-deoxybenanomicin A; C056805:benanomicin A; D000095643:Pradimicins and Benanomicins