Racemic synthesis of the new antibiotic tetramic acid reutericyclin

Authors
Marquardt, U Schmid, D Jung, G
Citation
U. Marquardt et al., Racemic synthesis of the new antibiotic tetramic acid reutericyclin, SYNLETT, (8), 2000, pp. 1131-1132
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
8
Year of publication
2000
Pages
1131 - 1132
Database
ISI
SICI code
0936-5214(200008):8<1131:RSOTNA>2.0.ZU;2-L
Abstract
The synthesis of the new bacteriocidal compound reutericyclin, 3-acetyl-1-( 2-trans-decenoyl)-2-hydroxy-5-isobutyl-Delta(2)-pyrrolin-4-one, is performe d by coupling of N-(2-trans-decenoyl)-L-leucine to Meldrum's acid followed by cyclization. The resulting N-acylated tetramic acid is directly C-acetyl ated in position 3. HPLC-purification on RP-C-18 gave racemic reutericyclin in high purity. 2D-NMR and FT-ICR-MS data are identical with those of natu ral reutericyclin.