Synthetic studies on d-biotin, part 9.1) An improved asymmetric synthetic route to d-biotin via Hoffmann-Roche lactone-thiolactone approach

Chemical and Pharmaceutical Bulletin

Volumn 53, Issue 7, 2005, Pages 743-746

  Chen, Fen Er ^a   Jia, Hui Qing ^a   Chen, Xu Xiang ^b   Dai, Hui Fang ^a   Xie, Bin ^a   Kuang, Yun Yan ^a   Zhao, Jian Feng ^a  

^a FUDAN UNIVERSITY   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Asymmetric reduction; d biotin; Desymmetrization; Polymer supported oxazaborolidine; Vitamin H; Wittig reaction

Indexed keywords

BIOTIN; DICARBOXYLIC ACID DERIVATIVE; IMIDE; OXAZABOROLIDINE DERIVATIVE; POLYMER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

BIOTIN; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFHYDRYL COMPOUNDS;

EID: 24944556143     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.53.743     Document Type: Article

References (39)

1. Chen F. E., Chen X. X., Dai H. F., Kuang Y. Y., Xie B. Zhao J. F., Adv. Synth. & Catal., 347, 549-554 (2005).
2. Mistry P. S., Dakshinamurti K., Vitam. Horm., 22, 1-55 (1964).
3. Maebashi M., Makino Y., Furukawa Y., Ohinata K., Kimura S., Sato T., J. Clin. Biochem, Nurt., 14, 211-218 (1993).
4. Coggeshall C. J., Heggers J. P., Robson C. M., Baker H., Ann. N.Y. Acad. Sci., 447, 389-392 (1985).
5. Parry R. J., Naidu M. V., Tetrahedron Lett., 21, 4783-4786 (1980).
6. Trainor D. A., Parry R. J., Gitterman A., J. Am. Chem. Soc., 102, 1467-1468 (1980).
7. Ahler M., Muller W., Reichert A., Ringsdorf H., Venzmer J., Angew. Chem., Int. Ed. Engl., 29, 1269-1285 (1990).
8. Marquet A., Frappier F., Guillerm G., Azoulav M., Florentin D., J. Am. Chem. Soc., 115, 2139-2145 (1993).
9. De Clercq P. J., Chem. Rev., 97, 1755-1792 (1997).
10. Shimizu T., Seki M., Tetrahedron Lett., 41, 5099-5101 (2000).
11. Shimizu T., Seki M., Tetrahedron Lett., 42, 429-432 (2001).
12. Shimizu T., Seki M., Tetrahedron Lett., 43, 1039-1042 (2002).
13. Mori Y., Seki M., Heterocycles, 58, 125-127 (2002).
14. Mori Y., Seki M., J. Org. Chem., 68, 1571-1574 (2003).
15. Seki M., Hatsuda M., Mori Y., Yamada S., Tetrahedron Lett., 43, 3269-3272 (2002).
16. Seki M., Mori Y., Hatsuda M., Yamada S., J. Org. Chem., 67, 5527-5536 (2002).
17. Seki M., Shimizu T., Inubushi K., Synthesis, 2003, 361-364 (2003).
18. Mori Y., Kimura M., Seki M., Synthesis, 2003, 2311-2316 (2003).
19. Seki M., Kimura M., Hatsuda M., Yoshida S., Shimizu T., Tetrahedron Lett., 44, 8905-8907 (2003).
20. Kimura M., Seki M., Tetrahedron Lett., 45, 1635-1637 (2004).
21. Kimura M., Seki M., Tetrahedron Lett., 45, 3219-3223 (2004).
22. Uskokovic M. R., "Encyclopedia of Chemical Technology," 3rd ed., Vol. 24, ed. by Kirk D. E., Othmer D. E., Wiley, New York, 1984, pp.41-49.
23. Chen F. E., Yuan J. L., Dai H. F., Kuang Y. Y., Chu Y., Synthesis, 2003, 2155-2160 (2003).
24. We noticed that the polymer-supported chiral sulfonamide was partially decomposed in the sixth cycle in the enantioselective reduction of 4 into 5. This made the work-up procedure very difficult to carry out and recycling of the polymer inefficient.
25. Price M. O., Sui J. K., Kurth M. J., Schore N. E., J. Org. Chem., 67, 8086-8089 (2002).
26. Zhao G., Hu J. B., Qian Z. S., Yin W. X., Tetrahedron: Asymmetry, 13, 2095-2098 (2002).
27. Itsuno S., Ito K., J. Chem, Soc, Perkin Trans I, 1984, 2887-2893 (1984).
28. Brown H. C., Jadhav P. K., Mandal A. K., Tetrahedron, 37, 3547-3587 (1981).
29. Apsimo J. W., Sequin R. P., Tetrahedron, 35, 2797-2842 (1979).
30. Itsuno S., Matsumoto T., Sato D., Inoue T., J. Org. Chem., 65, 5879-5881 (2000).
31. Felder M., Giffels G., Wandrey C., Tetrahedron: Asymmetry, 8, 1975-1977 (1997).
32. Itsuno S., Nakano M., Ito K., J. Chem. Soc. Perkin Trans. I, 1985, 2615-2619 (1985).
33. Aoki Y., Suzuki H., Akiyama H., Akano S., U.S. Patent, 3 876 659 (1975) [Chem. Abstr. 80, 95951z (1974)].
34. Ohashi N., Ikeda T., Shimage K., Takakashi T., Ishizumi K., Eur. Patent Appl., EP 84 377 (1983) [Chem. Abstr. 100, 34338q (1983)].
35. Chen F. E., Huang Y. D., Fu H., Cheng Y., Zhang D. M., Li Y. Y., Peng Z. Z., Synthesis, 2000, 2004-2008 (2000).
36. Chen F. E., Dai H. F., Kuang Y. Y., Jia H. Q., Tetrahedron: Asymmetry, 14, 3667-3672 (2003).
37. Yamano T., Tokuyama S., Aoki I., Nishiguchi Y., Nakahama K., Takanohashi T., Bull. Chem. Soc. Jpn., 66, 1456-1460 (1993).
38. Hirata N., Miyamoto Y., Mizuno M., Takahashi T., Mizuno T., Jpn. Kokai Tokkyo Koho JP 188247 (1996) [Chem. Abstr. 124, 8815u (1996)].
39. Takahash T., Minai M., Yamamoto T., Mizuno T., Miyamoto Y., Eur. Pat. Appl., EP 0633 263 (1995) [Chem. Abstr. 122, 187270r (1995)].