Substituted piperazines are found in a large variety of drugs such as antidepressants, anxiolytics, anthelminthes agents, antibiotics and antihistamines and possess very low acute toxicity in mammal.1 We are interesting by the synthesis of Rhodotorulic acid (RA) analogues. RA is a tetradentate piperazine siderophore produced by Rhodotorula piliman�2 that possesses two hydroxamate ligands with a (3S, 6S) stereochemistry to chelate ferric iron. In continuation of precedent work concerning the development of efficient and stereoselective di-substituted 2-oxopiperazines,3 we present here the stereoselective synthesis of 3,5 and 3,6 di-alkylated piperazine substituted by hydroxamate or catechol moieties. (1)        (a) Foguet, 1989,   US: 4859675. (b) Colglazier, M. L. et al. The Journal of Parasitology 1960  , 46, 267�270. (c) Coban, A. Y. et al. Current Microbiology 2010  , 62, 508.(2)        M�ller, G. et al. Journal of Biological Chemistry 1985  , 260, 13916.(3)        Lencina, C. L. et al. Tetrahedron: Asymmetry 2008  , 19, 1689.

Asymmetric synthesis of potential siderophores di-alkylated piperazine analogs

244th National Meeting (2012)

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