Total Synthesis of 3(S)-Carboxy-4(S)-hydroxy-2,3,4,5-tetrahydropyridazine, an Unusual Amino Acid Constituent of Luzopeptin A

Article abstract of DOI:10.1021/jo00275a007

The enantiospecific synthesis of 3(S)-carboxy-4(S)-hydroxy-2,3,4,5-tetrahydropyridazine (2), a novel constituent of the antibiotic antitumor agent luzopeptin A is described.Structural corroboration of the synthetic compound is based on three points.The 13C NMR spectrum of synthetic 2 was compared with that of a similar degradation product of luzopeptin.The 1H NMR spectrum of 2 was compared with that of the synthetic cis isomer.Finally, the synthetic methodology developed for the synthesis of 2 was applied to the synthesis of the known L-trans-3-hydroxyproline.