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http://dx.doi.org/10.5012/bkcs.2009.30.1.163

Stereoselective Synthesis of Diverse α-Hydroxy-β-amino Acids and It's Application for Synthesis of Dipeptide Expecting as a Protease Inhibitor  

Jang, Sang-Hun (Department of Chemistry and Research Institute of Life Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
Kim, Ju-Young (Department of Chemistry and Research Institute of Life Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
Kim, Min-Kyu (Department of Chemistry and Research Institute of Life Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
Han, Jeong-Woo (Department of Chemistry and Research Institute of Life Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
Park, Ki-Hun (Department of Agricultural Chemistry and Division of Applied Life Science, Gyeongsang National University)
Yoon, Yong-Jin (Department of Chemistry and Research Institute of Natural Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
Lee, Sang-Gyeong (Department of Chemistry and Research Institute of Life Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.1, 2009 , pp. 163-171 More about this Journal
Abstract
Few $\alpha$-Hydroxy-$\beta$-amino acids were synthesized via various nucleophilic addition of the epoxide and followed by stereoselective nucleophilic substitution reaction and eliminative cleavage of the acetal selectively in diacetal compound. One of the synthesized $\alpha$-Hydroxy-$\beta$-amino acid reacted with L-leucine methylester to give corresponding dipeptide in good yields.
Keywords
$\alpha$-Hydroxy-$\beta$-amino acids; Nucleophilic addition; Epoxide ring opening; Eliminative cleavage;
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1 Lee, J. H.; Lee, B. W.; Jang, K. C.; Jeong, I. Y.; Yang, M. S.; Lee, S. G.; Park, K. H. Synthesis 2003, 829   DOI   ScienceOn
2 Park, S. H.; Lee, H. W. Bull. Korean Chem. Soc. 2008, 29, 1447   DOI   ScienceOn
3 Enantioselective Synthesis of ${\beta}-Amino$ Acids; Eusebio Juaristi, Ed.; Wiley-VCH: New York, 1997
4 Rich, D. H. J. Med. Chem. 1985, 28, 263   DOI
5 Zhou, P.; Salleh, H.; Chan, P. C.; LaJiioe, G.; Honex, J. F.; Nambiar, P. T. C.; Ward, O. P. Carbohyd. Res. 1993, 239, 155   DOI
6 Lee, J. H.; Lee, B. W.; Jang, K. C.; Jeong, I. Y.; Yang, M. S.; Lee, S. G.; Park, K. H. Synthesis 2003, 829   DOI   ScienceOn
7 Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302   DOI   ScienceOn
8 Yates, M. H. Tetrahedron Lett. 1997, 38, 2813   DOI   ScienceOn
9 Branco, L. C.; Afonso, C. A. M. J. Org. Chem. 2004, 69, 4318   DOI   ScienceOn
10 Csuk, R.; Hugemer, M.; Vasella, A. Helv. Chim. Acta 1998, 71, 609   DOI
11 Chong, J. M.; Cry, D. R.; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009   DOI   ScienceOn
12 Alexakis, A.; Jachiet, D.; Normant, J. F. Tetrahedron 1986, 42, 5607   DOI   ScienceOn
13 Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329   DOI   ScienceOn
14 Green, T. W.; Wuts, P. G. M. Protective in Organic Synthesis, 2nd ed.; John Wiley &Sons, Inc.: 1991; p 67   DOI   ScienceOn
15 Park, K. H.; Yoon, Y. J.; Lee, S. G. Tetrahedron Lett. 1994, 35, 9737   DOI   ScienceOn
16 Molander, G. A.; Figueroa, R. Org. Lett. 2006, 8, 75   DOI   ScienceOn
17 Csuk, R.; Hugemer, M.; Vasella, A. Helv. Chim. Act. 1988, 71, 609   DOI
18 Lee, S. G.; Jeong, H. J. Bull. Korean Chem. Soc. 1998, 19, 598   DOI
19 Lee, S. G.; Lee, J. H. Bull. Korean Chem. Soc. 1997, 18, 556
20 Choudary, B. M.; Chodari, N. S.; Jyothi, K.; Kantam, M. L. J. Am. Chem. Soc. 2002, 124, 5341   DOI   ScienceOn
21 Tobe, H.; Morishima, H.; Takita, T.; Aoyagi, T.; Umezawa, H. Agr. Biol. Chem. 1979, 43, 591   DOI   ScienceOn
22 Juaristi, E.; Quintana, D.; Escalante, J. Aldrichimica Acta 1994, 27, 3
23 Aoyagi, T.; Tobe, H.; KoJma, F.; Hamada, M.; Takeuchi, T.; Umexawa, H. J. Antiobiot. 1978, 31, 221
24 Puiroux, J.; Loughton, B. G. Arch. of Insect Biochem. Phy. 1992, 19, 193   DOI   ScienceOn
25 Regeling, H.; de Rouville, E.; Chittenden, G. J. F. Recl. Trav. Chim. PaysBas 1987, 106, 461   DOI
26 Cole, D. C. Tetrahedron 1994, 50, 9517   DOI   ScienceOn
27 Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc. Perkin Trans. 1 1994, 2621
28 Mclnerney, B. V.; Taylor, W. C. Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science: Amsterdam, 1995; vol. 15, p 381
29 Iizuka, K.; KamiJo, T.; Harada, H.; Akhane, K.; Kubota, T.; Umeyama, H.; Kiso, Y. J. Chem. Soc. Chem. Commun. 1989, 1678
30 Hill, R. A. Prog. Chem. Org. Nat. Prod. 1986, 49, 1   DOI
31 Kobayashi, Y.; Takemoto, Y.; KamiJo, T.; Ito, Y.; Terashima, S. Tetrahedron 1992, 48, 1853   DOI   ScienceOn
32 OJima, I.; Park, Y. H.; Sun, S. M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737   DOI   ScienceOn
33 Hattoro, K.; Yamamoto, H. Tetrahedron 1994, 50, 2785   DOI   ScienceOn
34 Kobayashi, Y.; Takemoto, Y.; KamiJo, T.; Ito, Y.; Terashima, S. Tetrahedron 1990, 31, 3031   DOI   ScienceOn
35 Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; KamiJo, T.; Harada, H.; Terashima, S. Tetrahedron Lett. 1990, 48, 1853   DOI   ScienceOn
36 Inokuchi, T.; Tanigawa, S.; Kanazaki, M.; Torii, S. SynLett 1991, 701
37 Righi, G.; Rumboldt, G. J. Org. Chem. 1996, 61, 3557   DOI   ScienceOn
38 Pasto, M.; CasteJon, P.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1996, 61, 6033   DOI   ScienceOn
39 Maibaum, J.; Rich, D. H. J. Org. Chem. 1988, 53, 689   DOI
40 Morishma, H.; Umezawa, H. J. Antibiotics 1973, 26, 115   DOI