Problem statement: CoQ 10 is a key compound in ATP synthesis having wide number of health application especially for treating humans suffering from pathophysiological condition. The CoQ 10 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 CoQ 10 (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 CoQ 10 -quinol. Finally CAN oxidation of dimethyl quinol followed by purification yielded CoQ 10 in 13% overall yield. Conclusion: The present process achieved CoQ 10 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.
Isolation and characterisation of two new eudesmanolides, 5α-hydroperoxy-7α-hydroxy-isosphaerantholide (1) and (11α,13-dihydro-7α-hydroxyfrullanolide-13-yl)-adenine (2) from the flower heads of Sphaeranthus indicus are described. In addition, 5α-hydroxy-isosphaerantholide (3) and 11α,13-dihydro-eudesman-3,5,7-triene-6α-12-olide (4) are reported first time as a metabolite of S. indicus and as a natural product, respectively. The structures of these compounds were established from rigorous analysis of their high-resolution mass, IR, UV, H NMR,C NMR and 2D NMR spectral data.
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