Aminoglycoside Antibiotics [Paperback]

With contributions by numerous experts1 The Naturally Occurring Aminoglycoside Antibiotics.- A. Introduction.- B. Aminoglycoses and Noncyclitol Aminoglycosides.- I. Aminoglycose Derivatives.- II. Disaccharides and Pseudodisaccharides.- III. Trisaccharides.- C. Aminocyclitol Aminoglycosides Containing Streptamine, 2-Deoxystreptamine, or Their Derivatives.- I. Monosubstituted Streptamine and 2-Deoxystreptamine Aminoglycosides.- 1. 4- or 6-Substituted Cyclitol.- 2. 5-Substituted Cyclitol.- II. Disubstituted 2-Deoxystreptamine Aminoglycosides.- 1. 4,5-Disubstituted Cyclitol.- 2. 4,6-Disubstituted Cyclitol.- III. 1-N-Acyl Substituted Cyclitol.- D. Aminoglycosides with Cyclitol Aglycones Other than Streptamine or 2-Deoxystreptamine.- I. Nonbasic Cyclitol.- II. Monoaminocyclitol.- III. Diaminocyclitol.- References.- 2 Total Synthesis and Chemical Modification of the Aminoglycoside Antibiotics.- A. Introduction.- B. Several Reactions and Methods Generally Useful for the Synthesis of Aminoglycoside Antibiotics.- I. Simultaneous Protection of Vicinal Trans-Equatorial Amino and Hydroxyl Groups.- II. Selective Cyclic Acetalation.- III. 1,2-cis-Glycosylation of Aminosugars.- IV. Selective Deoxygenation Reactions.- 1. 3-Deoxygenation.- 2. 3,4-Dideoxygenation.- V. Selective N-Protection via Temporary Metal Chelation of Vicinal and Nonvicinal Amino-Hydroxy or Amino-Amino Groups.- VI. Determination of the Configurations of Aminopyranosides and Aminocyclitols by the Shift in Optical Rotation Due to Copper(II) Chelate Formation.- C. Total Synthesis and Modification of Aminoglycoside Antibiotics.- I. Streptomycin Group.- 1. Total Synthesis of Streptomycin and Dihydrostreptomycin.- 2. Chemical Modification of Streptomycin and Dihydrostreptomycin.- II. Pseudodisaccharides Containing 4-Substituted 2-Deoxystreptamine  Paromamine, Neamine, and Related Compounds.- 1. Synthesis of Paromamine and Neamine.- 2. Deoxygenated Derivatives.- 3. Epimerized Derivatives.- 4. Amino-Deoxy Derivatives.- lC$