Novel syntheses of the benzoquinones Idebenone and CoQ10

The topic of this project is related to the investigation, design and development of novel synthetic methods and pathways to natural antioxidants and their synthetic analogues that can be utilized as pharmaceuticals, nutraceuticals and preservation agents for food and feed, particularly marine lipids. Distinctive interest is paid to the development and exploration of phenolic and benzoquinone class of compounds such as coenzyme Q10 (CoQ10) and Idebenol. Focal point is the development of practical, efficient, and cost-effective synthetic methods and pathways that will employ cheap and readily available materials, and "green" conditions and reagents. A novel total synthesis to Idebenone is concluded while the development of a synthetic path leading to CoQ10 has also been explored. Among the deliverables are: a) a novel "green" bromination protocol for activated arenes b) an oxidation protocol leading to two versatile intermediates c) a purification protocol of Heck coupling post-reaction mixtures for transition metal catalyst based on organic solvent nanofiltration and d) a palladium catalyzed Heck coupling protocol performed under microwave irradiation.