Discrimination of spermidine amino functions by a new protecting group strategy; application to the synthesis of guanidinylated polyamines, including hirudonine

Abstract

Agmatine and hirudonine, guanidine derivatives of putrescine and spermidine, respectively, are synthesised by the application of a new protecting group strategy for polyamines, which uses N-nitroguanidinyl as a precursor of guanidine functions and selectively blocks spermidine at N-1 and N-8 with trifluoroacetyl and at N-4 by 4-azidobenzyloxycarbonyl.