Efficient and Flexible Solid-Phase Synthesis of N-Hydroxypolyamine Derivatives

Orthogonally protected, N-hydroxylated, linear tri- and tetra- amines were efficiently synthesised on Merrifield resin, which was modified with a phenethyl bromide linker. The polyamine frameworks were convergently prepared from the centre with reductive aminations and nucleophilic substitutions to elongate the polyamine backbone. The required N-hydroxy groups were introduced during the cleavage of the polyamine derivatives from the resin through Cope elimination. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)