Studies on the synthesis of (2S,3R)-3-hydroxy-3-methylproline via C 2-N bond formation

Journal of Organic Chemistry

Volumn 68, Issue 19, 2003, Pages 7479-7484

  Shen, Jun Wei ^a   Qin, Dong Guang ^a   Zhang, Hong Wang ^a   Yao, Zhu Jun ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYLATION; STEREOCHEMISTRY; SUBSTRATES; SYNTHESIS (CHEMICAL);

LEWIS ACIDS;

ORGANIC COMPOUNDS;

3 HYDROXY 3 METHYLPROLINE; CARBAMIC ACID ESTER; CARBON; DELTA CARBAMATE ALPHA,BETA EPOXIDE ESTER; LEWIS ACID; NITROGEN; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL BOND; DIASTEREOISOMER; DIHYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0141566423     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0349328     Document Type: Article

References (22)

1. (a) Kim, J.; Park, E. J. Curr. Med. Chem. Anti-Cancer Agents 2002, 2, 485-537.
2. (b) Cragg, G. M.; Newman, D. J.; Snader, K. M. J. Nat. Prod. 1997, 60, 53.
3. (a) Umezawa, K.; Nakazawa, K.; Uemura, T.; Ikeda, Y.; Kondo, S.; Naganawa, H.; Kinoshita, N.; Hashizume, H.; Hamada, M.; Takeuchi, T.; Ohba, S. Tetrahedron Lett. 1998, 39, 1389-1392.
4. (b) Umezawa, K.; Nakazawa, K.; Ikeda, Y.; Naganawa, H.; Kando, S. J. Org. Chem. 1999, 64, 3034-3038.
5. (a) Umezawa, K.; Nakazawa, K.; Uchihata, Y.; Otsuka, M. Adv. Enzyme Regul. 1999, 39, 145-156.
6. (b) Chen, W. H.; Horoszewicz, J. S.; Leong, S. S.; Shimano, T.; Penetrante, R.; Sanders, W. H.; Berjian, R.; Douglass, H. O.; Martin, E. W.; Chu, T. M. In Vitro 1982, 18, 24.
7. Noguchi, Y.; Uchiro, H.; Yamada, T.; Kobayashi, S. Tetrahedron Lett. 2001, 42, 5253.
8. Makino, K.; Kondoh, A.; Hamada, Y. Tetrahedron Lett. 2002, 43, 4695.
9. Qin, D.-G.; Zha, H.-Y.; Yao, Z.-J. J. Org. Chem. 2002, 67, 1038-1040.
10. Qin, D.-G.; Yao, Z.-J. Tetrahedron Lett. 2003, 44, 571-574.
11. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5 765.
12. (a) Sivakumar, M.; Borhan, B. Tetrahedron Lett. 2003, 44, 5547.
13. (b) Hatakeyama, S.; Sakurai, K.; Numata, H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201-5203.
14. (c) Fujiwara, K.; Tokiwano, T.; Murai, A.; Tetrahedron Lett. 1995, 36, 8063-8066.
15. (a) Hodgson, D. M.; Glen, R.; Redgrave, A. J. Tetrahedron Lett. 2002, 43, 3927-3930.
16. (b) Toyooka, N.; Okumura, M.; Himiyama, T.; Nakazawa, A.; Nemoto, H. Synlett 2003, 55-58.
17. (a) Cortes, M.; Razmilic, I.; Lopez, J.; Leyton, F. Bull. Soc. Chim. Belg. 1989, 98, 417-418.
18. (b) Kodama, M.; Minami, H.; Mima, Y.; Fukuyama, Y.; Tetrahedron Lett. 1990, 31, 4025-4026.
19. (c) Yasuda, M.; Ide, M.; Matsumoto, Y.; Nakata, M. Synlett 1997, 899-902.
20. Andrus, M. B.; Li, W.; Keyes, R. F. J. Org. Chem. 1997, 62, 5542-5549.
21. Blaney, P.; Grigg, R.; Rankovic, Z.; Thorntonpett, M.; Xu, J. Tetrahedron 2002, 58, 1719-1738.
22. Buchstaller, H.-P.; Siebert, C. D.; Lyssy, R. H.; Frank, I.; Duran, A.; Gottschlich, R.; Noe, C. R. Monatsh. Chem. 2001, 132, 279-294.