Semisynthetic routes to PF1022H--A precursor for new derivatives of the anthelmintic cyclooctadepsipeptide PF1022A

Sivatharushan Sivanathan; Florian Körber; Jürgen Scherkenbeck

doi:10.1016/j.bmc.2016.01.014

Semisynthetic routes to PF1022H--A precursor for new derivatives of the anthelmintic cyclooctadepsipeptide PF1022A

Bioorg Med Chem. 2016 Feb 15;24(4):873-6. doi: 10.1016/j.bmc.2016.01.014. Epub 2016 Jan 8.

Authors

Sivatharushan Sivanathan¹, Florian Körber¹, Jürgen Scherkenbeck²

Affiliations

¹ Department of Chemistry, University of Wuppertal, Gaußstraße 20, 42119 Wuppertal, Germany.
² Department of Chemistry, University of Wuppertal, Gaußstraße 20, 42119 Wuppertal, Germany. Electronic address: Scherkenbeck@uni-wuppertal.de.

PMID: 26810834
DOI: 10.1016/j.bmc.2016.01.014

Abstract

The cyclooctadepsipeptide PF1022A and its semisynthetic, commercial analogue emodepside show excellent anthelmintic properties. Bis-hydroxy PF1022 (PF1022H), a minor fermentative side-product represents an interesting precursor for new PF1022 related anthelmintics. We report herein two complementary routes which allow a highly efficient conversion of PF1022A to a regioisomeric mixture consisting mainly of the bis-para isomer PF1022H and the meta-para analogue.

Keywords: Anthelmintic; Baeyer–Villiger oxidation; Cylooctadepsipeptide; PF1022H.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anthelmintics / chemical synthesis*
Anthelmintics / chemistry
Depsipeptides / chemical synthesis*
Depsipeptides / chemistry
Oxidation-Reduction
Peptides, Cyclic / chemical synthesis*
Peptides, Cyclic / chemistry
Stereoisomerism

Substances

Anthelmintics
Depsipeptides
Peptides, Cyclic
PF 1022A
emodepside