AN EFFICIENT SYNTHESIS OF ORTHOGONALLY PROTECTED SPERMIDINE

ABSTRACT

A major problem in the use of spermidine for the synthesis of biologically interesting compounds is the selective orthogonal protection of the three different amino groups. Our approach is based on the Fukuyama reaction, starting from putrescine and 3-amino-1-propanol and affording N ⁸-benzyloxycarbonyl-N ¹-tert-butyloxycarbonyl-N ⁴-(2-nitrobenzenesulfonyl)spermidine (5) in 5 steps in high yield.

ACKNOWLEDGMENTS

The authors are grateful to the Fund of Scientific Research – Flanders (Belgium), the INCO program of the European Community and the Flemisch Community for support. K. Amssoms is a fellow of the Institute for the Promotion of Innovation by Science and Technology in Flanders (IWT).