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http://dx.doi.org/10.5012/bkcs.2007.28.9.1545

Efficient Construction of Quaternary Carbon: Stereocontrolled Synthesis of Novel Abacavir Analogue  

Kim, Ai-Hong (BK-21 Project Team, College of Pharmacy, Chosun University)
Hong, Joon-Hee (BK-21 Project Team, College of Pharmacy, Chosun University)
Publication Information
Bulletin of the Korean Chemical Society / v.28, no.9, 2007 , pp. 1545-1548 More about this Journal
Abstract
This paper discusses the racemic and stereoselective synthetic route for novel 4'α -methyl and 6'α -methyl analogues of abacavir. The quaternary carbon at the 4'-position of carbocyclic nucleoside was installed successfully via a Claisen rearrangement. The stereocontrolled construction of a methyl group in the 6'α - position was directed through the Felkin-Anh rule. A Bis-vinyl compound 9 was cyclized successfully using Grubbs' catalyst II to provide a carbocycle nucleus for the target compound. The synthesized compound 15 showed moderate anti-HIV activity (EC50 = 10.67 μM, MT-4 cell lines).
Keywords
Quaternary carbon; Abacavir; Claisen rearrangement; Ring-closing metathesis;
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Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 6  (Related Records In Web of Science)
Times Cited By SCOPUS : 6
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1 Daluge, S. M.; Good, S. S.; Faletto, M. B.; Miller, W. H.; St Clair, M. H.; Boone, L. R.; Tisdale, M.; Parry, N. R.; Reardon, J. E.; Dornsife, R. E.; Averett, D. R.; Krenitsky, T. A. Antimicrob. Agents Chemother. 1997, 41, 1082
2 Levine, S.; Hernandez, D.; Yamanaka, G.; Zhang, S.; Rose, R.; Weinheimer, S.; Colonno, R. J. Antimicrob. Agents Chemother. 2002, 46, 2525   DOI   ScienceOn
3 Furster, A. Angew. Chem. Int. Ed. 2003, 39, 3012   DOI   ScienceOn
4 Palmer, J. L.; Abeles, R. H. J. Biol. Chem. 1979, 254, 1217
5 Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S.; Earl, R. A. Tetrahedron 1994, 50, 10611   DOI   ScienceOn
6 Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571   DOI   ScienceOn
7 Herdewijn, P.; De Clercq, E.; Balzarini, J.; Vanderhaeghe, H. J. Med. Chem. 1985, 28, 550   DOI
8 Ueland, P. M. Pharmacol. Rev. 1982, 34, 223
9 Sugimoto, I.; Shuto, S.; Mori, S.; Shigeta, S.; Matuda, A. Bioorg. Med. Chem. Lett. 1999, 9, 285   DOI   ScienceOn
10 Ohrui, H.; Kohgo, S.; Kitano, K.; Sakata, S.; Kodama, E.; Yoshimura, K.; Matsuoka, M.; Shigeta, S.; Mitsuya, H. H. J. Med. Chem. 2000, 43, 4516   DOI   ScienceOn
11 Katagiri, N.; Nomura, M.; Sato, H.; Kaneko, C.; Yusa, K.; Tsuruo, T. J. Med. Chem. 1992, 35, 1882   DOI
12 Tanaka, M.; Norimine, Y.; Fujita, T.; Suemune, H.; Sakai, K. J. Org. Chem. 1996, 61, 6952   DOI   ScienceOn
13 Hong, J. H.; Ko, O. H. Bull. Korean Chem. Soc. 2003, 24, 1284   DOI   ScienceOn
14 Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P. J. Virol Methods 1988, 20, 309   DOI   ScienceOn
15 McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239   DOI   ScienceOn
16 Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191   DOI   ScienceOn
17 Crimmins, M. T.; King, B. W.; Zuercher, W. J.; Choy, A. L. J. Org. Chem. 2000, 65, 8499   DOI   ScienceOn