N-Methylpseudoephedrine-mediated asymmetric syntheses of O-carboxyalkylated flavones

Heterocycles

Volumn 71, Issue 5, 2007, Pages 1163-1171

  Kang, Kyoung Hee ^a   Heo, Ji Hyeon ^a   Kim, Yongtae ^a   Park, Yong Sun ^a  

^a Konkuk University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547498562     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-07-11022     Document Type: Article

References (20)

1. Middleton E., Kandaswamy C., and Theoharides T.C. Pharmacol. Rev. 52 (2000) 673
2. Havsteen B.H. Pharmacol. Ther. 96 (2002) 67
3. Babu K.S., BAbu T.H., Srinivas P.V., Kishore K.H., Murthy U.S.N., and Rao J.M. Bioorg. Med. Chem. Lett. 16 (2006) 221
4. Mughal E.U., Ayaz M., Hussain Z., Hasan A., Sadiq A., Riaz M., Malik A., Hussain S., and Choudhary M.I. Bioorg. Med. Chem. 14 (2006) 4704
5. Comte G., Daskiewicz J.-B., Bayet C., Conseil G., Viornery-Vanier A., Dumontet C., Pietro A.D., and Barron D. J. Med. Chem. 44 (2001) 763
6. Gao G.-Y., Li D.-J., and Keung W.M. J. Med. Chem. 44 (2001) 3320
7. Shin J.-S., Kim K.-S., Kim M.-B., Jeong J.-H., and Kim B.-K. Bioorg. Med. Chem. Lett. 9 (1999) 869
8. Setnikar I., and Ravasi M. Nature 183 (1959) 898
9. Tobe M., Isobe Y., Goto Y., Obara F., Tsuchiya M., Matsui J., Hirota K., and Hayashi H. Bioorg. Med. Chem. 8 (2000) 2037
10. Auffret G., Labaied M., Frappier F., Rasoanaivo P., Grellier P., and Lewin G. Bioorg. Med. Chem. Lett. 17 (2007) 959
11. Chung H.J., Choi Y.H., Choi H.D., Jang J.M., Shim H.J., Yoo M., Kwon J.W., and Lee M.G. Eur. J. Pharm. Sci. 27 (2006) 363
12. Kim K.-T., Moon S.-H., Yeo E.-J., Park Y.S., Han Y.-S., Na S.-Y., Lee N.G., and Paik H.-D. Food Sci. Biotechnol. 15 (2006) 466
13. Nam J., Lee S.-k., and Park Y.S. Tetrahedron 59 (2003) 2397. 6. Both (S,S)- and (R,R)-N-methylpseudoephedrine are commercially available and also can be easily prepared by N-methylation of pseudoephedrine with formaldehyde and formic acid.
14. Lee S.-k., Nam J., and Park Y.S. Synlett (2002) 790. 6. Both (S,S)- and (R,R)-N-methylpseudoephedrine are commercially available and also can be easily prepared by N-methylation of pseudoephedrine with formaldehyde and formic acid.
15. Nam J., Lee S.-k., Kim K.Y., and Park Y.S. Tetrahedron Lett. 42 (2002) 8253. 6. Both (S,S)- and (R,R)-N-methylpseudoephedrine are commercially available and also can be easily prepared by N-methylation of pseudoephedrine with formaldehyde and formic acid.
16. For reviews on DTR, see. Kim Y., Shin E.-k., Beak P., and Park Y.S. Synthesis (2006) 3805. 8. In references 5a-c, we have established that (R)-products were provided in the substitution of (S,S)-N-methylpseudoephedrine α-bromoacetates with various nucleophiles. We confirmed that the absolute configuration of (R)-5 by comparison of CSP-HPLC retention time with authentic product prepared from commercially available (S)-α-bromopropionic acid. The absolute configurations of O-carboxyalkylated flavones 3-4 and 6-13 are provisionally assigned by analogy.
17. Park Y.S., Yum E.K., Basu A., and Beak P. Org. Lett. 8 (2006) 2667. 8. In references 5a-c, we have established that (R)-products were provided in the substitution of (S,S)-N-methylpseudoephedrine α-bromoacetates with various nucleophiles. We confirmed that the absolute configuration of (R)-5 by comparison of CSP-HPLC retention time with authentic product prepared from commercially available (S)-α-bromopropionic acid. The absolute configurations of O-carboxyalkylated flavones 3-4 and 6-13 are provisionally assigned by analogy.
18. Coldham I., Dufour S., Haxell T.F.N., Howard S., and Vennall G.P. Angew. Chem. Int. Ed. 41 (2002) 3887. 8. In references 5a-c, we have established that (R)-products were provided in the substitution of (S,S)-N-methylpseudoephedrine α-bromoacetates with various nucleophiles. We confirmed that the absolute configuration of (R)-5 by comparison of CSP-HPLC retention time with authentic product prepared from commercially available (S)-α-bromopropionic acid. The absolute configurations of O-carboxyalkylated flavones 3-4 and 6-13 are provisionally assigned by analogy.
19. Clayden J., Mitjans D., and Youssef L.H. J. Am. Chem. Soc. 124 (2002) 5266. 8. In references 5a-c, we have established that (R)-products were provided in the substitution of (S,S)-N-methylpseudoephedrine α-bromoacetates with various nucleophiles. We confirmed that the absolute configuration of (R)-5 by comparison of CSP-HPLC retention time with authentic product prepared from commercially available (S)-α-bromopropionic acid. The absolute configurations of O-carboxyalkylated flavones 3-4 and 6-13 are provisionally assigned by analogy.
20. Nakamura S., Nakagawa R., Watanabe Y., and Toru T. J. Am. Chem. Soc. 122 (2000) 11340. 8. In references 5a-c, we have established that (R)-products were provided in the substitution of (S,S)-N-methylpseudoephedrine α-bromoacetates with various nucleophiles. We confirmed that the absolute configuration of (R)-5 by comparison of CSP-HPLC retention time with authentic product prepared from commercially available (S)-α-bromopropionic acid. The absolute configurations of O-carboxyalkylated flavones 3-4 and 6-13 are provisionally assigned by analogy.