Catalytic asymmetric total synthesis of (S)-(-)-zearalenone, a novel lipoxygenase inhibitor

Marc P Baggelaar; Yange Huang; Ben L Feringa; Frank J Dekker; Adriaan J Minnaard

doi:10.1016/j.bmc.2013.06.024

Catalytic asymmetric total synthesis of (S)-(-)-zearalenone, a novel lipoxygenase inhibitor

Bioorg Med Chem. 2013 Sep 1;21(17):5271-4. doi: 10.1016/j.bmc.2013.06.024. Epub 2013 Jun 20.

Authors

Marc P Baggelaar¹, Yange Huang, Ben L Feringa, Frank J Dekker, Adriaan J Minnaard

Affiliation

¹ Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.

PMID: 23867388
DOI: 10.1016/j.bmc.2013.06.024

Abstract

A catalytic asymmetric synthesis of (S)-(-)-zearalenone is reported using asymmetric allylic alkylation for the introduction of the stereocenter. (S)-(-)-Zearalenone turned out to be a novel lipoxygenase inhibitor.

Keywords: (S)-(−)-Zearalenone; Allylic alkylation; Lipoxygenase; Mycotoxin; Resorcyclic acid lactone.

Publication types

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

MeSH terms

Alkylation
Catalysis
Kinetics
Lipoxygenase / chemistry*
Lipoxygenase / metabolism
Lipoxygenase Inhibitors / chemical synthesis*
Lipoxygenase Inhibitors / chemistry
Lipoxygenase Inhibitors / metabolism
Protein Binding
Stereoisomerism
Zearalenone / chemical synthesis*
Zearalenone / chemistry
Zearalenone / metabolism

Substances

Lipoxygenase Inhibitors
Zearalenone
Lipoxygenase