Stereoselective synthesis of L-deoxyaltronojirimycin from L-serine

Bulletin of the Korean Chemical Society

Volumn 30, Issue 7, 2009, Pages 1531-1534

  Rengasamy, Rajesh ^a   Curtis Long, Marcus J ^b   Ryu, Hyung Won ^a   Oh, Kyeong Yeol ^a   Park, Ki Hun ^a  

^a Gyeongsang National University   (South Korea)

^b NONE   (United Kingdom)

Author keywords

Azasugars; L deoxyaltronojirimycin; Polyhydroxylated piperidine; Ring closing metathesis; Vinyl magnesium bromide

Indexed keywords

AZASUGARS; L-DEOXYALTRONOJIRIMYCIN; POLYHYDROXYLATED PIPERIDINE; RING CLOSING METATHESIS; VINYL MAGNESIUM BROMIDE;

ADDITION REACTIONS; ALDEHYDES; AMINES; AMINO ACIDS; AROMATIC HYDROCARBONS; HYDROXYLATION; MAGNESIUM; METHANOL; STEREOCHEMISTRY; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

EID: 69249162741     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2009.30.7.1531     Document Type: Article

References (30)

1. Azenevo, P. B.; Creemer, L. J.; Daniel, J. K.; King, C. H. R.; Liu, P. S. J. Org. Chem. 1989, 54, 2539.
2. Butters, T. D.; Dwek, R. A.; Platt, F. M. Glycobiology 2005, 15, 43R.
3. Wu, S.-F.; Lee, C.-J.; Liao, C.-L.; Dwek, R. A.; Zitzmann, N.; Lin, Y.-L. J. Virol. 2002, 76, 3596.
4. Gross, P. E.; Baker, M. A.; Carver, J. P.; Dennis, J. W. Clin. Cancer Res. 1995, 1, 935.
5. Butters, T. D.; Dwek, R. A.; Platt, F. M. Chem. Rev. 2000, 100, 4683.
6. Kim, J. H.; Long, M. J. C.; Kim, J. Y.; Park, K. H. Org. Lett. 2004, 6, 2273.
7. Kim, J. H.; Curtis-Long, M. J.; Seo, W. D.; Ryu, Y. B.; Yang, M. S.; Park, K. H. J. Org. Chem. 2005, 70, 4082.
8. Jang, K. C.; Choi, S. J.; Kim, J. H.; Lee, J. H.; Lee, B. W.; Park, K. H. Bull. Korean Chem. Soc. 2003, 24, 921.
9. Miyake, Y.; Ebata, M. J. Antibiot. 1987, 40, 122.
10. Kato, A.; Asano, N.; Kizu, H.; Matsui, K.; Watson, A. A.; Nash, R. J. J. Nat. Prod. 1997, 60, 312.
11. Taylor, C. M.; Barker, W. D.; Weir, C. A.; Park, J. H. J. Org. Chem. 2002, 67, 4466.
12. Taylor, C. M.; Weir, C. A. Org. Lett. 1999, 1, 787.
13. Non-carbohydrates: (c) Delair, P.; Brot, E.; Kanazawa, A.; Greene, A. E. J. Org. Chem. 1999, 64, 1383.
14. Martin, R.; Alcon, M.; Pericas, M. A.; Riera, A. J. Org. Chem. 2002, 67, 6896.
15. An, J. N.; Meng, X. B.; Yao, Y.; Li, Z. J. Carbohydrate Res. 2006, 341, 2200.
16. Rengasamy, R.; Curtis-Long, M. J.; Seo, W. D.; Jeong, S. H.; Jeong, I.-Y.; Park, K. H. J. Org. Chem. 2008, 73, 2898.
17. For similar protocols using N,N-dibenzyl amino aldehydes and Garner's aldehyde: Reetz, M. T. Chem. Rev. 1999, 99, 1121.
18. Takahata, H.; Banba, Y.; Sasatani, M.; Nemoo, H.; Kato, A.; Adachi, I. Tetrahedron 2004, 60, 8199.
19. Takahata, H.; Banba, Y.; Ochi, H.; Nemoto, H. Org. Lett. 2003, 5, 2527.
20. Ferreira, F.; Botuha, C.; Chemla, F.; Perez-Luna, A. J. Org. Chem. 2008, 74, 2238.
21. Mengle, A.; Reiser, O. Chem. Rev. 1999, 99, 1191.
22. Hong, S. H.; Sanders, D. P.; Lee, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 17160.
23. Moise, J.; Arseniyadis, S.; Cossy, J. Org. Lett. 2007, 9, 1695.
24. For the relative selectivities and rates in epoxidation of cyclohex-2-en-1-ol and cyclohex-3-en-1-ol, see: Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136.
25. Chamberlain, P.; Roberts, M. L.; Whitham, G. H. J. Chem. Soc. Perkin 1 1970, 1374.
26. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
27. Henbest, H. B.; Wilson, R. A. L. J. Chem. Soc. 1957, 1958.
28. Takahata, H.; Banba, Y.; Ouchi, H.; Nemato, H.; Kato, A.; Adachi, I. J. Org. Chem. 2003, 68, 3603.
29. Kato, A.; Kato, N.; Kano, E.; Adachi, I.; Ikeda, K.; Yu, L.; Okamoto, T.; Banba, Y.; Ouchi, H.; Takahata, H.; Asano, N. J. Med. Chem. 2005, 48, 2036.
30. Sowmy Reddy, M.; Narender, M.; Rama Rao, K. Tetrahedron 2007, 63, 8199.