Highly diastereoselective epimerization: Stereodivergent synthesis of α-hydroxy-β-amino isopentanoic acid

Journal of Organic Chemistry

Volumn 71, Issue 13, 2006, Pages 5008-5011

  Seo, Woo Duck ^a   Curtis Long, Marcus J ^b   Ryu, Young Bae ^a   Lee, Jin Hwan ^a   Yang, Min Suk ^a   Lee, Woo Song ^c   Park, Ki Hun ^a  

^a Gyeongsang National University   (South Korea)

^b Trout Beck   (United Kingdom)

^c Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

Α-HYDROXY-Β-AMINO ISOPENTANOIC ACID; ENANTIOPURE; EPIMERIZATION; OXAZOLIDIN-2-ONE;

CATALYST ACTIVITY; DERIVATIVES; HYDROLYSIS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

AMINO ACIDS;

ALPHA HYDROXY BETA AMINOISOPENTANOIC ACID; BASE; CARBOXYLIC ACID DERIVATIVE; FUNCTIONAL GROUP; METHYL 3 BENZYL 4 ISOPROPYL 2 OXOOXAZOLIDINE 5 CARBOXYLATE; METHYL 4 ISOPROPYL 2 OXOOXAZOLIDINE 5 CARBOXYLATE; OXAZOLIDIN 2 ONE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; DIASTEREOISOMER; EPIMERIZATION; HYDROLYSIS; ISOMER; STEREOCHEMISTRY; SYNTHESIS;

MOLECULAR CONFORMATION; OXAZOLIDINONES; PENTANOIC ACIDS; STEREOISOMERISM;

EID: 33745436272     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060309m     Document Type: Article

References (37)

1. (a) Kotake, T.; Rajesh, S.; Yoshio, H.; Mukai, Y.; Ueda, M.; Kimura, T.; Kiso, Y. Tetrahedron Lett. 2004, 45, 3651-3654.
2. (b) Guenard, D.; Gueritte-Voegelein, F.; Potier, P. Acc. Chem. Res. 1993, 26, 160-167.
3. (c) Zhao, Y.; Jiang, N.; Chen, S.; Peng, C.; Zhung, X.; Zou, Y.; Zhang, S.; Wang, J. Tetrahedron 2005, 61, 6546-6552.
4. (d) Harada, T.; Inui, C. J. Org. Chem. 2006, 71, 1277-1279.
5. (a) Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Ishida, T.; Kiso, Y. J. Med. Chem. 1990, 33, 2707-2714.
6. (b) Boger, J.; Lohr, N. S.; Ulm, E. H.; Poe, M.; Blaine, E. H.; Fanelli, G. M.; Lin, T. Y.; Payne, L. S.; Schorn, T. W.; Lamont, B. I.; Vassil, T. C; Stabilito, I. I.; Veber, D. F.; Rich, D. H.; Bopari, A. S. Nature 1983, 303, 81-84.
7. (c) Rich, D. H.; Moon, B. J.; Boparai, A. S. J. Org. Chem. 1980, 45, 2288-2290.
8. (d) Nezami, A.; Luque, I.; Kimura, T.; Kiso, Y.; Freire, E. Biochemistry 2002, 41, 2273-2280.
9. (a) Righi, G.; Rumboldt, G. J. Org. Chem. 1996, 61, 3557-3560.
10. (b) Ha, H. J.; Park, G. S.; Ahn, Y. G.; Lee, G. S. Bioorg. Med. Chem. Lett. 1998, 8, 1619-1622.
11. (c) Cardillo, G.; Tolomelli, A.; Tomasini, C. Tetrahedron 1995, 51, 11831-11840.
12. (a) Wee, A. G. H.; McLeod, D. D. J. Org. Chem. 2003, 68, 6268-6273.
13. (b) Shuto, D.; Kasai, S.; Kimura, T.; Liu, P.; Hidaka, K.; Hamada, T.; Shibakawa, S.; Hayashi, Y.; Hattori, C.; Szabo, B.; Ishiura, S.; Kiso, Y. Bioorg. Med. Chem. Lett. 2003, 13, 4273-4276.
14. (a) Herranz, R.; Castro-Pichel, J.; Vinuesa, S.; Garcia-Lopez, M. T. J. Org. Chem. 1990, 55, 2232-2234.
15. (b) Gill, D. M.; Pegg, N. A.; Rayner, C. M. Tetrahedron Lett. 1995, 45, 8237-8330.
16. For a review, see: (a) Bergmeier, S. C. Tetrahedron 2000, 56, 2561-2576.
17. (b) Liu, Mei.; Sibi, M. P. Tetrahedron 2002, 58, 7991-8035.
18. (a) Denis, J. N.; Greene, A. E.; Serra, A. A.; Luche, M. J. J. Org. Chem. 1986, 51, 46-50.
19. (b) Deng, L.; Jacobsen, E. N. J. Org. Chem. 1992, 57, 4320-4323.
20. (a) Rubin, A. E.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2637.
21. (b) Donohoe, T. J.; Johnson, P. D.; Pye, R. J. Org. Biomol. Chem. 2003, 1, 2025-2028.
22. Lee, B. W.; Lee, J. H.; Jang, K. C.; Kang, J. E.; Kim, J. H.; Park, K. M.; Park, K. H. Tetrahedron Lett. 2003, 44, 5905-5907.
23. Kudyba, I.; Raczko, J.; Jurczak, J. J. Org. Chem. 2004, 69, 2844-2850.
24. (a) Denis, J. N.; Correa, A.; Greene, A. E. J. Org. Chem. 1991, 56, 6939-6942.
25. (b) Manickam, G.; Nogami, H.; Kanai, M.; Groger, H.; Shibasaki, M. Synlett 2001, 5, 617-620.
26. (a) Hagihara, M.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6570-6573.
27. (b) Iwanowicz, E. J.; Lin, J.; Robert, D. G. M.; Michael, I. M.; Seiler, S. M. Bioorg. Med. Chem. Lett. 1992, 2, 1607-1612.
28. Seo, W. D.; Curtis-Long, M. J.; Kim, J. H.; Park, J. K.; Park, K. M.; Park, K. H. Synlett 2005, 15, 2289-2292.
29. (a) Disadee, W.; Ishikawa, T. J. Org. Chem. 2005, 70, 9399-9406.
30. (b) Davis, S. G.; Fenwick, D. R.; Ichihara, O. Tetrahedron: Asymmetry 1997, 5, 3387-3391.
31. (a) Golebiowski, A.; Jacobsson, U.; Raczko, J.; Jurczak, J. J. Org. Chem. 1989, 54, 3759-3760.
32. (b) Ginesta, X.; Pericas, M. A.; Riera, A. Synth. Commun. 2005, 35, 289-297.
33. (a) Mohan, R.; Chou, Y. L.; Bihovsky, R.; Lumma, W. C.; Erhardt, P. W., Jr.; Shaw, K. J. J. Med. Chem. 1991, 34, 2402-2410.
34. (b) Peet, N. P.; Burkhart, J. P.; Angelastro, M. R.; Giroux, E. L.; Mehdi, S.; Bey, P.; Kolb, M.; Neises, B.; Schirlin, D. J. Med. Chem. 1990, 33, 394-407.
35. (a) Miyata, O.; Koizumi, T.; Asai, H.; Iba, R.; Naito, T. Tetrahedron 2004, 60, 3893-3914.
36. (b) Kobayashi, S.; Isobu, T.; Ohno, M. Tetrahedron Lett. 1984, 25, 5079-5082.
37. Mazaleyrat, J. P.; Goubard, Y.; Azzini, M. V.; Wakselman, M.; Peggion, C.; Formaggio, F.; Toniolo, C. Eur. J. Org. Chem. 2002, 1232-1247.