Aminoglycoside Antibiotics — Modified, Enantiopure Sannamine‐ and Sporamine‐Type Glycosyl Acceptors

Along an established scheme, 1,2:3,4‐dianhydrodeoxy‐epi‐inositol (3) — readily available from benzene — has been applied to expeditious syntheses of suitably protected, fluorinated, and epimerized aminoglycoside building blocks related to sannamine (rac‐14a, rac‐16a, rac‐18a, rac‐31a) and sporamine (rac‐21a, rac‐23a, rac‐26a, rac‐34a). By separation of diastereomers formed with (+)‐(1‐phenylethyl)amine (14c/ 14′c; 16c/16'c) or with (‐)‐camphanic acid (14e/14'e) and by enzymatic hydrolysis (rac‐14b) access is gained to enantiopure glycosyl acceptors. Aminoglycosid‐Antibiotica ‐‐‐ Modifizierte, enantiomerenreine Glycosyl‐Acceptoren vom Sannamin‐ und Sporamin‐Typ Aminoglycoside Antibiotics ‐‐‐ Modified, Enantiopure Sannamine‐ and Sporamine‐Type Glycosyl Acceptors