Synthesis of Coenzyme Q10

Ravada, Suryachandra Rao; Emani, Lakshma Reddy; Garaga, Machi Raju; Meka, Bharani; Golakoti, Trimurtulu
April 2009
American Journal of Infectious Diseases;2009, Vol. 5 Issue 2, p83
Academic Journal
Problem statement: CoQ10 is a key compound in ATP synthesis having wide number of health application especially for treating humans suffering from pathophysiological condition. The CoQ10 presently available in the market is solely derived from fermentation process. A commercially viable synthetic process is yet to be realized. Approach: The researchers described a new synthetic route for the preparation of CoQ10 (1). This new process utilized inexpensive isoprenol as a precursor for the synthesis of an early intermediate with a single isoprene unit. Another key step was the selective oxidation of trans methyl of isoprene unit as a prelude to the expansion of the side chain to decaprenyl group using solanesol. Results: Prenylation of 2, 3-dimethoxy-5-methylhydroquinone using isoprenol in presence of a Lewis acid, followed by selective oxidation of trans methyl group of isoprenyl side chain and subsequent allylic bromination yielded a bromide precursor (7). The ptoluenesulfination of the bromide followed by coupling with solanesyl bromide and de-ptoluenesulfination yielded dimethyl derivative of the CoQ10-quinol. Finally CAN oxidation of dimethyl quinol followed by purification yielded CoQ10 in 13% overall yield. Conclusion: The present process achieved CoQ10 starting from a relatively inexpensive precursor. Further improvement in the coupling reaction between 8 and solanesyl bromide may lead to a better and viable synthetic process.


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