Initially, it was our plan to tosylate the alcohol of 16 and to displace it with an appropriate hydride source (Scheme 5A). Accordingly, tosylate 17 was prepared by stirring 16 with NEt3 and TsCl. However, despite multiple trials, including with NaBH4, LiAlH4, and NaBH3CN, we were unable to cleanly obtain 18, likely because of the presence of an azide functionality. We thus sought to develop a protocol which would allow for the clean formation of the methyl group and the primary amine of kasugamine in a single step. Knowing that there was precedent for the Pd-catalyzed hydrogenolysis of azides and alkyl iodides, we prepared iodide 19 using a Finkelstein reaction (Scheme 5B). Indeed, stirring 19 with NEt3 and Pd-C under an atmosphere of H2 gas cleanly delivered kasugamine derivative 20. Crystal structure analysis of 20 (CCDC 2291427) allowed us to unambiguously confirm its identity and absolute stereochemistry.