A Concise and Efficient Total Synthesis of Oleocanthal

作者：Valli Matteo; Peviani Elena Giulia; Porta Alessio; D' Alfonso Alessandro; Zanoni Giuseppe; Vidari Giovanni^*

来源：European Journal of Organic Chemistry, 2013, 2013(20): 4332-4336.

DOI：10.1002/ejoc.201300324

• Olive oil
• Total synthesis
• Synethtic methods
• Terpenoids
• Natural products

%26lt;title content-type=%26quot;main%26quot;%26gt;Abstract %26lt;br%26gt;Oleocanthal, one of the minor components of the phenolic fraction isolated from extra virgin olive oil, is an effective inhibitor of COX enzymes, possessing similar potency to the NSAID ibuprofen. Moreover, it has the capacity to alter the structure of neurotoxic A-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 materials. Moreover, resolution of the racemic mixture on an HPLC chiral column provided both enantiomers of oleocanthal in a single operation for biological studies.

• 出版日期2013-7