Synthesis of (3R,10R)- and (3S,10S)-Diastereomers of 3,10-Dimethylspermine

A simple and practical 10-step synthesis is reported for previously unknown diastereomers of C‑methylated spermine (Spm) analogue, 1,12-diamino-3,10-dimethyl-4,9-diazadodecane (3,10-Me2Spm), starting from commercially available enantiomers of 2-(Boc-amino)-1-propanol. Title compounds were prepared in gram scale, in excellent overall yields and enantiomeric purity. Since biochemical properties of 3,10‑Me2Spm can be regulated by changing the configuration of chiral center(s), these analogues are of obvious value for studying not only cellular functions of spermine, but even diseases associated with the disturbances of spermine metabolism.