Bioorganic & Medicinal Chemistry Letters 2006-08-15

Synthesis and anthelmintic activity of substituted (R)-phenyllactic acid containing cyclohexadepsipeptides.

Peter Jeschke, Jordi Benet-Buchholz, Achim Harder, Winfried Etzel, Michael Schindler, Wolfgang Gau, Hans-Christoph Weiss

Index: Bioorg. Med. Chem. Lett. 16(16) , 4410-5, (2006)

Full Text: HTML

Abstract

The substituted (R)-phenyllactic acid containing cyclohexadepsipeptides (CHDPs) represent novel enniatin derivatives with strong in vivo activities against the parasitic nematode Haemonchus contortus Rudolphi in sheep. 2D NMR spectroscopic analysis revealed for the substituted (R)-phenyllactic acid containing CHDPs one major conformer with an unsymmetrically folded conformation lacking a cis-amide bond. A correlation between the substitution pattern and its anthelmintic activity was found. Here we report on a simple total synthetic pathway of the precursor for this particular type of CHDPs and an efficient modification of the benzylic side chain (R-PhLac(2)).