Oleocanthal, one of the minor components of the phenolic fraction isolated from extra virgin olive oil, is an effective in- hibitor of COX enzymes, possessing similar potency to the NSAID ibuprofen. Moreover, it has the capacity to alter the structure of neurotoxic Aβ-amyloid oligomers (ADDLs) and to change the structure of deformed microtubule-associated tau–protein, thus inhibiting the formation of neurofibrillary tangles. It can have, therefore, potential therapeutic use for the treatment of neurodegenerative diseases. In this paper we describe the total synthesis of ()-oleocanthal in just 8 steps (9 % overall yield) from easily available starting materi- als. Moreover, resolution of the racemic mixture on an HPLC chiral column provided both enantiomers of oleocanthal in a single operation for biological studies.

A Concise and Efficient Total Synthesis of Oleocanthal

VALLI, MATTEO;PEVIANI, ELENA GIULIA;PORTA, ALESSIO;D'ALFONSO, ALESSANDRO;ZANONI, GIUSEPPE;VIDARI, GIOVANNI
2013

Abstract

Oleocanthal, one of the minor components of the phenolic fraction isolated from extra virgin olive oil, is an effective in- hibitor of COX enzymes, possessing similar potency to the NSAID ibuprofen. Moreover, it has the capacity to alter the structure of neurotoxic Aβ-amyloid oligomers (ADDLs) and to change the structure of deformed microtubule-associated tau–protein, thus inhibiting the formation of neurofibrillary tangles. It can have, therefore, potential therapeutic use for the treatment of neurodegenerative diseases. In this paper we describe the total synthesis of ()-oleocanthal in just 8 steps (9 % overall yield) from easily available starting materi- als. Moreover, resolution of the racemic mixture on an HPLC chiral column provided both enantiomers of oleocanthal in a single operation for biological studies.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11571/717620
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