Facile synthesis of monoacetylated spermidines, illustrating selective deacetylation and application of a common precursor.
The synthesis of all three monoacetylated spermidines is reported. N4-Acetylspermidine was obtained in four steps from spermidine via the triacetylated intermediate by selective deacetylation after exhaustive t-butoxycarbonylation as well as directly from a previously described protected precursor. N1-Acetylspermidine and N8-acetylspermidine were both obtained in four simple protection/deprotection steps from a common, selectively protected compound, thus illustrating the versatility of the latter.
Lurdes
M
M
Department of Biochemistry, University of Uppsala, Sweden.
Almeida
S
S
Grehn
L
L
Ragnarsson
U
U
D003640:Dealkylation; D007202:Indicators and Reagents; D013095:Spermidine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; C030223:N(8)-acetylspermidine; C017988:N(1)-acetylspermidine; C067717:N(4)-acetylspermidine; C067716:N(1)-benzyloxycarbonyl-N(8)-butoxycarbonylspermidine; D013095:Spermidine