A Concise and Efficient Total Synthesis of Oleocanthal. Issue 20 (23rd May 2013)

• Record Type: Journal Article
• Authors: Valli, Matteo; Peviani, Elena Giulia; Porta, Alessio; D'Alfonso, Alessandro; Zanoni, Giuseppe; Vidari, Giovanni
• Is Part Of: European journal of organic chemistry. Issue 20(2013)
• Page Start: 4332
• Page End: 4336
• Publication Date: 2013-05-23
• Subjects: Olive oil -- Total synthesis -- ­Synethtic methods -- Terpenoids -- Natural products; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300324
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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 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 materials. Moreover, resolution of the racemic mixture on an HPLC chiral column provided both enantiomers of oleocanthal in a single operation for biological studies. Abstract : Oleocanthal, a component of extra virgin olive oil, possesses anti‐inflammatory activity and inhibits the formation of neurofibrillary tangles. In this paper, we have achieved the shortest synthesis of (±)‐oleocanthal reported so far from easily available starting materials. Chiral chromatographic resolution of the mixture provided both enantiomers for biological studies.