Synthesis of demethyl derivatives of istamycin A.
- 1 January 1980
- journal article
- research article
- Published by Japan Antibiotics Research Association in The Journal of Antibiotics
- Vol. 33 (11) , 1281-1288
- https://doi.org/10.7164/antibiotics.33.1281
Abstract
4-N,6''-N,3-O-Tridemethylistamycin A0 (9) and 6''-N,3-O-didemethylistamycin A0 (15) were synthesized from 3,2'',6''-tri-N-benzyloxycarbonyl-3'',4''-dideoxyneamine-1,6-carbamate (1) through an aziridine derivative (6) by an analogous procedure employed in the total synthesis of istamycin A0 (19). Acylation of 15 with glycine at the 4-methylamino group gave 6''-N,3-O-didemethylistamycin A (18) having interesting activities especially against Pseudomonas, but 4-N,6''-N,3-O-tridemethylistamycin A (12) derived from 9 showed only weak activity. The 4-N-methyl group of istamycin A (20) is essential for the antimicrobial activity.This publication has 1 reference indexed in Scilit:
- Fortimicins A and B, new aminoglycoside antibiotics. III. Structural identification.The Journal of Antibiotics, 1977