title: Selective deoxygenation and O-methylation of benanomicin A: synthesis of 9-deoxy-, 9-O-methyl- and 14-O-methylbenanomicin A.
abstract: 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.
authors.affiliation: Institute of Microbial Chemistry, M. C. R. F., Tokyo, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Nishizuka
authors.forename: S
authors.initials: S
authors.lastname: Hirosawa
authors.forename: M
authors.initials: M
authors.lastname: Hamada
authors.forename: S
authors.initials: S
authors.lastname: Kondo
authors.forename: D
authors.initials: D
authors.lastname: Ikeda
authors.forename: T
authors.initials: T
authors.lastname: Takeuchi
mesh_terms: 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
chemical_list: 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