New synthesis of chiral 1,3-oxazinan-2-ones from carbohydrate derivatives

Journal of Organic Chemistry

Volumn 70, Issue 2, 2005, Pages 463-469

  Ella Menye, Jean Rene ^a   Sharma, Vibha ^a   Wang, Guijun ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATES; CARBONYLATION; DERIVATIVES; DRUG PRODUCTS; SYNTHESIS (CHEMICAL);

AMINO ALCOHOLS; CARBOHYDRATE DERIVATIVES; SYNTHETIC METHOD;

AROMATIC HYDROCARBONS;

1,3 OXAZINAN 2 ONE; 3 BENZYL 5 (2 (METHYLAMINO)ETHYL)OXAZOLIDIN 2 ONE; 3 ETHYL 6 ((TRITYLOXY)METHYL) 1,3 OXAZINAN 2 ONE; 3 ETHYL 6 (HYDROXYMETHYL) 1,3 OXAZINAN 2 ONE; 3 HYDROXY GAMMA BUTYROLACTONE; 3 METHYL 6 ((TRITYLOXY)METHYL) 1,3 OXAZINAN 2 ONE; 5 (AMINOMETHYL) 2 OXAZOLIDINONE; 5 (HYDROXYMETHYL) 2 OXAZOLIDINONE; 6 ((BENZYLAMINO)METHYL) 3 ETHYL 1,3 OXAZINAN 2 ONE; 6 ((TRITYLOXY)METHYL) 1,3 OXAZINAN 2 ONE; 6 (BENZYLAMINO)METHYL) 3 METHYL 1,3 OXAZINAN 2 ONE; 6 (HYDROXYMETHYL) 3 METHYL 1,3 OXAZINAN 2 ONE; 6 HYDROXYMETHYL 1,3 OXAZINAN 2 ONE; 6 PHENYL 1,3 OXAZINAN 2 ONE; AMIDE; AMINE; AMINOALCOHOL; ANTIINFECTIVE AGENT; ASPARTIC ACID; CARBAMIC ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE; EPEREZOLID; LACTONE; LINEZOLID; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ALLERGY; ARTHRITIS; ARTICLE; ASTHMA; CARBONYLATION; CHEMICAL STRUCTURE; CHIRALITY; DIABETES MELLITUS; DRUG STRUCTURE; DRUG SYNTHESIS; INFLAMMATORY DISEASE; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; SYNTHESIS; TECHNIQUE; ULCER;

4-BUTYROLACTONE; AMIDES; AMINES; AMINO ALCOHOLS; CARBOHYDRATES; DRUG DESIGN; MOLECULAR STRUCTURE; OXAZINES;

EID: 12344317936     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040224q     Document Type: Article

References (40)

1. Hollingsworth, R. I.; Wang, G.; Padmakumar, R.; Mao, J.; Zhang, H.; Dai, Z.; Puthuparampil, K. PCT Int. Appl. WO03106413 A, 2003; Chem. Abstr. 2003, 140, 59633.
2. Hollingsworth, R. I.; Wang, G.; Padmakumar, R.; Mao, J.; Zhang, H.; Dai, Z.; Puthuparampil, K. PCT Int. Appl. WO03106413 A, 2003; Chem. Abstr. 2003, 140, 59633.
3. Pittelkow, T.; Fischer, E.; Treppendahl, S. P. PCT Int. Appl. WO 2001087837, 2001; Chem. Abstr. 2001, 136, 5898.
4. Pittelkow, T.; Fischer, E.; Treppendahl, S. P. PCT Int. Appl. WO 2001087837, 2001; Chem. Abstr. 2001, 136, 5898.
5. Brickner, S. J. Curr. Pharm. Design 1996, 2, 175-194.
6. Barbachyn, M. R.; Ford, C. W. Angew. Chem., Int. Ed. 2003, 42, 2010-2023.
7. Perrault, W. R.; Pearlman, B. A.; Godrej, D. B.; et al. Org. Process Res. Dev. 2003, 7, 533-546.
8. Wang, G.; Hollingsworth, R. I. Tetrahedron: Asymmetry 2000, 11, 4429-4432.
9. Hollingsworth, R. I.; Wang, G. Chem. Rev. 2000, 100, 4267-4282.
10. Bernet, B.; Bishop, P. M.; Caron, M.; Kawamata, T.; Roy, B. L.; Ruest, L.; Sauve, G.; Soucy, P.; Deslongchamps, P., Can. J. Chem. 1985, 63, 2818-2820.
11. Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E.; Au-Yeung, B.-W.; Balaram, P.; Browne, L. J.; Card, P. J.; Chen, C. H.; Chenevert, R. B.; Fliri, A.; Frobel, K.; et al. J. Am. Chem. Soc. 1981, 103, 3213-3215.
12. Baenteli, R.; Bauer, W.; Cottens, S.; Ehrhardt, C.; Hommel, U.; Kallen, J.; Meingassner, J. G.; Nuninger, F.; Weitz-Schmidt, G. PCT Int. Appl. WO 0048989, 2000; Chem. Abstr. 2000, 133, 177065.
13. Baenteli, R.; Bauer, W.; Cottens, S.; Ehrhardt, C.; Hommel, U.; Kallen, J.; Meingassner, J. G.; Nuninger, F.; Weitz-Schmidt, G. PCT Int. Appl. WO 0048989, 2000; Chem. Abstr. 2000, 133, 177065.
14. Gormley, G., Jr.; Chan, Y. Y.; Fried, J. J. Org. Chem. 1980, 45, 1447-1454.
15. Larson, G. M.; Schaneberg, B. T.; Sneden, A. T. J. Nat. Prod. 1999, 62, 361-363.
16. Cassady, J. M.; Chan, K. K.; Floss, H. G.; Leistner, E. Chem. Pharm. Bull. 2004, 52, 1-26.
17. Yamana, K.; Suzuki, N.; Takahama, A.; Ine, S. Jpn. Kokai Tokkyo Koho JP 2002179572, 2002; Chem. Abstr. 2002, 137, 57555.
18. Yamana, K.; Suzuki, N.; Takahama, A.; Ine, S. Jpn. Kokai Tokkyo Koho JP 2002179572, 2002; Chem. Abstr. 2002, 137, 57555.
19. Jin, F.; Confalone, P. N. PCT Int. Appl. (119 pp) WO 2000000481, 2000; Chem. Abstr. 2000, 132, 78560.
20. Jin, F.; Confalone, P. N. PCT Int. Appl. (119 pp) WO 2000000481, 2000; Chem. Abstr. 2000, 132, 78560.
21. Takiguchi, T.; Iwaki, T.; Tokanou, G.; Kosaka, Y.; Nakamura, S. JP9151179, 1997; Chem. Abstr. 1997, 127, 42427.
22. Takiguchi, T.; Iwaki, T.; Tokanou, G.; Kosaka, Y.; Nakamura, S. JP9151179, 1997; Chem. Abstr. 1997, 127, 42427.
23. Abbas, T. R.; Cadogan, J. I. G.; Doyle, A. A.; Gosney, I.; Hodgson, P. K. G.; Howells, G. E.; Hulme, A. N.; Parsons, S.; Sadler, I. H. Tetrahedron Lett. 1997, 38, 4917-4920.
24. Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Gould, R. O.; Hodgson, K. G.; McDougall, D. Tetrahedron 1998, 54, 9765-9784.
25. Poindexter, G. S.; Strauss, K. M. Synth. Commun. 1993, 23, 1329-1338.
26. Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. Chem. Lett. 1988, 87-90.
27. Lohray, B. B.; Baskaran, S.; Reddy, B. Y.; Rao, K. S. Tetrahedron Lett. 1998, 39, 6555-6556.
28. Ross, B. C. U.S. Patent 4107435, 1977; Chem. Abstr. 1977, 88, 7304.
29. Ross, B. C. U.S. Patent 4107435, 1977; Chem. Abstr. 1977, 88, 7304.
30. Fujita, M.; Kitagawa, O.; Suzuki, T.; Taguchi, T. J. Org. Chem. 1997, 62, 7330-7335.
31. Jorda-Gregori, J. M.; Gonzalez-Rosende, M. E.; Cava-Montesinos, P.; Sepulveda-Arques, J.; Galeazzi, R.; Orena, M. Tetrahedron: Asymmetry 2000, 11, 3769-3777.
32. Muehlstaedt, M.; Meusinger, R.; Olk, B.; Weber, L.; Widera, R. J. Prakt. Chem. 1986, 328, 309-313.
33. Dewynter, G.; Abdaoui, M.; Regainia, Z.; Montero, J.-L. Tetrahedron 1996, 52, 14217-14224.
34. Sonoda, N.; Yamamoto, G.; Natsukawa, K.; Kondo, K.; Murai, S. Tetrahedron Lett. 1975, 16, 1969-1972.
35. Kemp, S. J.; Bao, J. G.; Pedersen, S. F. J. Org. Chem. 1996, 61, 7162-7167.
36. Hirama, M.; Nishizaki, I.; Shigemoto, T.; Itô, S. J. Chem. Soc., Chem. Commun. 1986, 393-394.
37. Walsh, P. J.; Bennani, Y. L.; Sharpless, K. B. Tetrahedron Lett. 1993, 34, 5543-5548.
38. Hilborn, J. W.; Lu, Z.-H.; Jurgens, A. R.; Fang, Q. K.; Byers, P.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 2001, 42, 8919-8921.
39. Hollingsworth, R. I. Biotech. Annu. Rev. 1996, 2, 281-287.
40. Wang, G.; Hollingsworth, R. I. J. Org. Chem. 1999, 64, 1036-1038.