Our synthesis of (+)-kasugamycin commenced with commercially available 2-butyn-1-ol, which was reduced into (E)-2-buten-1-ol (1) using lithium aluminum hydride (Scheme 2). The corresponding chloride was prepared using triphenylphosphine and hexachloroacetone (modified Appel conditions). Sharpless dihydroxylation gave chloro-diol 3 in a 63% yield and 89% ee. Treatment of 3 with NaOH gave an epoxy-alcohol which was converted into the corresponding TBS ether prior to purification. This epoxide was regioselectively opened using cis-1-propenylmagnesium bromide and CuI. Resulting alcohol 5 was sulfamoylated using conditions developed by Sguazzin, Johnson, and Magolan. Sulfamate 6 was subjected to our laboratory's aza-Wacker cyclization reaction, giving oxathiazinane 7 in an excellent yield and as a single diastereomer (within limits of 1 H NMR detection) (Scheme 3). 7 was activated by appending a Cbz group and ring-opened using NaN3. 9 was unstable in acidic NMR solvents but was readily di-hydroxylated using K2OsO4•2H2O and NMO. The diol was cleaved using NaIO4. In one-pot, the TBS group was removed using pTsOH and cyclization of the resulting aldose gave kasugamine derivative 11 as a mixture of anomers. The anomeric OH group was converted into the corresponding acetate using Ac2O/pyridine/DMAP. The acetate was exchanged with thiophenol using BF3•OEt2. Enantiopure thioglycoside 13 crystallized along with its racemate, consistent with the observed % ee for 3, and both were confirmed by X-ray diffraction analysis (CCDC 2335847 and CCDC 2353400). We note that this is enantioselective synthesis of a kasugamine derivative is much improved (10 steps) relative to our first chiral-pool attempt (~17 steps from a literature compound). available 1D-chiro-inositol was converted into its tris-acetonide derivative using 2,2-dimethoxypropane and catalytic pTsOH (Scheme 4). One of these acetonides was selectively removed using aqueous acetic acid to give C2-symmetric diol 15. 15 was mono-benzylated using NaH and BnBr in DMF.