Enantioselective synthesis of (R)- and (S)-3-methylspermidines

Earlier unknown enantiomerically pure ( R )- and ( S )-1,8-diamino-3-methyl-4-azaoctane’s (3-MeSpd’s) were synthesized within 11 steps with high overall yields and optical purity starting from commercially available R - and S -isomers of N -Boc-2-aminopropanol-1. Application of R - and S -isomers of 3-MeSpd for the investigation of the stereospecificity of spermidine transporter and peculiarities of deoxyhypusine synthase reaction are discussed.