Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2014; 46(17): 2371-2375
DOI: 10.1055/s-0033-1338643
DOI: 10.1055/s-0033-1338643
paper
Two-Step Synthesis of 2-(9-Hydroxynonyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone
Further Information
Publication History
Received: 21 February 2014
Accepted after Revision: 23 April 2014
Publication Date:
28 May 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201417/lookinside/thumbnails/10.1055-s-0033-1338643-1.jpg)
Abstract
2-(9-Hydroxynonyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone was readily synthesized from commercially available 3,4,5-trimethoxytoluene in two steps. First, 2,3-dimethoxy-5-methyl-1,4-benzoquinone (coenzyme Q0) was obtained in one step by treatment of 3,4,5-trimethoxytoluene with hydrogen peroxide under metal-free conditions, followed by free-radical alkylation with 10-hydroxydecanoic acid in the presence of potassium peroxodisulfate and silver nitrate in a mixed solvent (MeCN–H2O, 1:1) to afford the title compound in good yields (60%, based on coenzyme Q0).
Key words
coenzyme Q0 - decarboxylative cross-coupling - idebenone analogue - free-radical alkylationSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
References
- 1 Current address: Université de Toulouse, Université Toulouse III - Paul Sabatier, le campus des science APPT 396, 1 impasse andre marfaing, 31400, Toulouse, France.
- 2a Tsoukala A, Bjørsvik H.-R. Org. Process Res. Dev. 2011; 15: 673
- 2b Geromel V, Darin N, Chrétien D, Bénit P, DeLonlay P, Rötig A, Munnich A, Rustin P. Mol. Genet. Metab. 2002; 77: 21
- 2c Yu C.-A, Yu L. Biochemistry 1982; 21: 4096
- 3a Asin-Cayuela J, Manas A.-RB, James AM, Smith RA. J, Murphy MP. FEBS Lett. 2004; 571: 9
- 3b Jung Y.-S, Joe B.-Y, Cho SJ, Konishi Y. Bioorg. Med. Chem. Lett. 2005; 15: 1125
- 3c Okamoto K, Watanabe M, Morimoto H, Imada I. Chem. Pharm. Bull. 1988; 36: 178
- 4a Wang J, Yang J, Yang B, Hu X, Sun J.-Q, Yang T. J. Chem. Res. 2010; 34: 717
- 4b Wang J, Yang J, Yang B, Sun J.-Q, Yang T. J. Chem. Res. 2010; 34: 724
- 4c Wang J, Yang J, Zhou R.-G, Yang B, Wu Y.-S. J. Chem. Res. 2011; 35: 431
- 4d Wang J, Yang J, Zhou R.-G, Yang B, Wu Y.-S. J. Chem. Res. 2011; 35: 428
- 4e Wang J, Zhou R.-G, Wu T, Yang T, Qin Q.-X, Li L, Yang B, Yang J. J. Chem. Res. 2012; 36: 121
- 5 Duveau DY, Arce PM, Schoenfeld RA, Raghav N, Cortopassi GA, Hecht SM. Bioorg. Med. Chem. 2010; 18: 6429
- 6a Goto G, Okamoto K, Okutani T, Isuke I. Chem. Pharm. Bull. 1985; 33: 4422
- 6b Lu L, Chen F. Synth. Commun. 2004; 34: 4049
- 6c Lipshutz BH, Lower A, Berl V, Schein K, Wetterich F. Org. Lett. 2005; 7: 4095
- 7 Jung Y.-S, Joe B.-Y, Seong C.-M, Park N.-S. Synth. Commun. 2001; 31: 2735
- 8a Liu B, Gu L, Zhang J. Recl. Trav. Chim. Pays-Bas 1991; 110: 104
- 8b Minisci F, Bernardi R, Bertini F, Galli R, Perchinummo M. Tetrahedron 1971; 27: 3575
- 8c Zhao W.-M, Chen X.-L, Yuan J.-W, Qu L.-B, Duan L.-K, Zhao Y.-F. Chem. Commun. 2014; 50: 2018
- 9a Palde PB, McNaughton BR, Ross NT, Gareiss PC, Mace CR, Spitale RC, Miller BL. Synthesis 2007; 2287
- 9b Duncton MA. J. Med. Chem. Commun. 2011; 2: 1135
- 10 Bernini R, Mincione E, Barontini M, Fabrizi G, Pasqualetti M, Tempesta S. Tetrahedron 2006; 62: 7733