Total synthesis of 3-O-demethylsporaricin A.
- 1 January 1985
- journal article
- research article
- Published by Japan Antibiotics Research Association in The Journal of Antibiotics
- Vol. 38 (11) , 1512-1525
- https://doi.org/10.7164/antibiotics.38.1512
Abstract
The novel, semisynthetic pseudodisaccharide antibiotic, 3-O-demethylsporaricin A, was synthesized via 3-O-demethylsporaricin B obtained by glycosidation of its aminocyclitol part. The aminocyclitol part was synthesized as D,L-form from D,L-(1,2,3/4,5,6)-bis(benzyloxycarbonylamino)-5,6-O-isopropylidene-2,3,5,6-cyclohexanetetraol via three key steps, namely, deoxygenation, inversion of a hydroxyl group, and N-methylation. The physical and biological properties of synthetic 3-O-demethylsporaricin A and an authentic sample derived from sporaricin B were identical.This publication has 6 references indexed in Scilit:
- In vitro and in vivo antibacterial activities of K-4619, a new semisynthetic aminoglycosideAntimicrobial Agents and Chemotherapy, 1984
- Lysinomicin, a new aminoglycoside antibiotic. II. Structure and stereochemistry.The Journal of Antibiotics, 1984
- A new broad-spectrum aminoglycoside antibiotic complex, sporaricin. III. The structures of sporaricins A and B.The Journal of Antibiotics, 1979
- A new broad-spectrum aminoglycoside antibiotic complex, sporaricin. II. Taxonomic studies on the sporaricin producing strain Saccharopolyspora hirsuta subsp. kobensis nov. subsp.The Journal of Antibiotics, 1979
- A NEW BROAD-SPECTRUM AMINOGLYCOSIDE ANTIBIOTIC COMPLEX, SPORARICINThe Journal of Antibiotics, 1979
- Fortimicins A and B, new aminoglycoside antibiotics. III. Structural identification.The Journal of Antibiotics, 1977