À)-(3S)-3-(Tosylamino)butano-4-lactone (1) and its derivative ethyl (À)-(3S)-4-iodo-3-(tosylamino)butanoate (2) are presented as easily accessible chiral building blocks for the construction of a range of different macrolactam frameworks important for the synthesis of naturally occurring polyamine alkaloids as well as for establishing a substance library of such compounds, including S-containing derivatives for biological tests. In addition to that, the absolute configuration of the spermine alkaloid (À)-(R)-budmunchiamine A (3) from Albizia amara was determined by total synthesis according to the new methodology.Scheme 2 a) PPh 3 , 1H-imidazole, I 2 , CH 2 Cl 2 , r.t., 1 h; 89%. b) t BuLi, Et 2 O, À 788 3 r.t., 2 h. c) CuBr ¥ Me 2 S, Et 2 O/THF, À 788 3À 208, 30 min. d) 2, Et 2 O/THF, À 608 3À 108, 3 h; 75%. e) H 2 N(CH 2 ) 4 NH 2 (10), Cu(OAc) 2 , r.t., 8 h; quant. f) TsCl, Et 3 N, CHCl 3 , r.t, 2 h; 93%. g) TsO(CH 2 ) 3 OTs (13), Cs 2 CO 3 , DMF, 658, 24 h, 78%.h) Electrolysis, EtOH, 58; 92%. Figure. ORTEP [14] Plot of the doubly N-tosylated macrolactam 14