SELECTIVE DEOXYGENATION AND O-METHYLATION OF BENANOMICIN-A - SYNTHESIS OF 9-DEOXYBENANOMICIN-A, 9-O-METHYLBENANOMICIN-A AND 14-O-METHYLBENANOMICIN-A

Authors
NISHIZUKA T HIROSAWA S HAMADA M KONDO S IKEDA D TAKEUCHI T
Citation
T. Nishizuka et al., SELECTIVE DEOXYGENATION AND O-METHYLATION OF BENANOMICIN-A - SYNTHESIS OF 9-DEOXYBENANOMICIN-A, 9-O-METHYLBENANOMICIN-A AND 14-O-METHYLBENANOMICIN-A, Journal of antibiotics, 50(9), 1997, pp. 765-769
Citations number
11
Categorie Soggetti
Pharmacology & Pharmacy",Immunology,"Biothechnology & Applied Migrobiology
Journal title
Journal of antibiotics → ACNP
ISSN journal
00218820
Volume
50
Issue
9
Year of publication
1997
Pages
765 - 769
Database
ISI
SICI code
0021-8820(1997)50:9<765:SDAOOB>2.0.ZU;2-0
Abstract
The selective modifications of phenolic hydroxy groups in the chromoph ore of benanomicin A are described. Hydride reduction of 9-O-tosylate with sodium borohydride/nickel chloride led to 9-deoxybenanomicin A. M ethylation of 1-O-diphenylmethylbenanomicin A diphenylmethyl ester wit h sodium hydride/iodomethane gave 9-O-methyl derivative and with HUNIG 'S base/diazotrimethylsilylmethane afforded the 14-O-methyl derivative . These compounds showed the diminished activity against fungi.