Efficient synthesis of nicotianamine and non-natural analogues

Abstract

An efficient synthesis of nicotianamine has been achieved by using a new strategy based on N-alkylation. Sulfonamide activation proved to be necessary for the alkylation of the primary amine and the 2-(trimethylsilyl)ethanesulfonyl group was easily introduced and found to provide the best compromise for the N-alkylation and deprotection reactions. This new strategy enabled the preparation of several unnatural analogues including original molecules that will be useful as tools for plant physiology studies. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.