Synthesis of anthelmintically activeN-methylated amidoxime analogues of the cyclic octadepsipeptide PF1022A
作者:Peter Jeschke、Achim Harder、Georg von Samson-Himmelstjerna、Winfried Etzel、Wolfgang Gau、Gerhard Thielking、Gerhard Bonse
DOI:10.1002/ps.590
日期:2002.12
product PF1022A. In particular an improved efficacy against Haemonchus contortus Rudolphi and Trichostrongylus colubriformis Giles in sheep compared to the potent cyclicoctadepsipeptidePF1022A and its mono-thionated derivative has been observed. Here we report on a specific modification at the N-methyl amide linkage by using the mono-thionated PF1022A, resulting in novel anthelmintically active backbone
polyhydroxylated azepanes. Polyheterocyclic scaffolds were prepared by intramolecular aza-[4+3] cycloadditionreactions of aza-oxyallylic cations with cyclic dienes. The aza-oxyallylic cation was generated in situ by the dehydrohalogenation of α-halohydroxamates. The highly functionalized heterocyclic products undergo a variety of reactions that provide useful scaffolds for target-directed synthesis, including