Racemic Synthesis of the New Antibiotic Tetramic Acid Reutericyclin

Udo Marquardt; Dietmar Schmid; Günther Jung

doi:10.1055/s-2000-6734

Synlett 2000; 2000(8): 1131-1132
DOI: 10.1055/s-2000-6734

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Racemic Synthesis of the New Antibiotic Tetramic Acid Reutericyclin

Udo Marquardt^* , Dietmar Schmid, Günther Jung

^*EMC microcollections, Sindelfinger Str. 3, 72072 Tübingen, Germany; Fax ++ 49 7071 29 5560; E-mail: guenther.jung@uni-tuebingen.de

Abstract

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The synthesis of the new bacteriocidal compound reutericyclin, 3-acetyl-1-(2-trans-decenoyl)-2-hydroxy-5-isobutyl-Δ²-pyrrolin-4-one, is performed by coupling of N-(2-trans-decenoyl)-l-leucine to Medlrum's acid followed by cyclization. The resulting N-acylated tetramic acid is directly C-acetylated in position 3. HPLC-purification on RP-C₁₈ gave racemic reutericyclin in high purity. 2D-NMR and FT-ICR-MS data are identical with those of natural reutericyclin.

antibiotics - acylation - Lewis acid catalysis - cyclization

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