2-deoxystreptamine: Central scaffold of aminoglycoside antibiotics

An overview of the synthetic routes aimed at (derivatives of) 2-deoxystreptamine in terms of retrosynthetic analysis to starting materials is given. The organic chemistry efforts are delineated in three segments: (a) collection of meso-2-deoxystreptamine and hydrosamine (methyl-2-deoxystreptamine) by degradation of neomycin or via synthetic routes; (b) enantiomerically pure protected derivatives of meso-2-deoxystreptamine, either by enzymatic resolution or from starting materials from the chiral pool; and (c) synthetic routes leading to regioisomers and dideoxy derivatives.