Tartaric Acid Derived Aziridines as Chiral Precursors of 3-Amino-3-deoxy and 2-Amino-2-deoxy Tetroses: An Efficient Approach Towards Mugineic Acid

F. Carreaux; A. Duréault; J. C. Depezay

doi:10.1055/s-1992-21403

Synlett 1992; 1992(6): 527-529
DOI: 10.1055/s-1992-21403

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Tartaric Acid Derived Aziridines as Chiral Precursors of 3-Amino-3-deoxy and 2-Amino-2-deoxy Tetroses: An Efficient Approach Towards Mugineic Acid

F. Carreaux^* , A. Duréault, J. C. Depezay

^*Université René Descartes, Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, URA 400 CNRS, 45 rue des Saints-Pères, F-75270 Paris Cedex 06, France

Abstract

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Protected forms of 3-amino-3-deoxy-D-erythrose 2 and of 2-amino-2-deoxy-L-erythrose 11 have been enantiospecifically prepared starting from the diethyl L-tartrate derived aziridine 1 through a Pummerer rearrangement. Compound 2 was shown to be a convenient chiral building block for the synthesis of the 4-[2-(2- benzyloxycarbonylazetidin-1-yl)-1-benzyloxyethyl]-3-tert-butoxycarbonyl -2, 2-dimethyl-1,3-oxazolidine 3, a precursor for mugineic acid.

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