A novel and practical synthesis of (+)-biotin via Fukuyama coupling reaction

Yakugaku Zasshi

Volumn 123, Issue 2, 2003, Pages 43-52

  Shimizu, Toshiaki ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

(+) Biotin; Fukuyama coupling reaction; L aspartic acid; Thiolactone

Indexed keywords

ASPARAGINE DERIVATIVE; ASPARTIC ACID; BIOTIN; BUTYROLACTONE; IMIDAZOLIDINE DERIVATIVE; LACTONE; CARBON; LEAD; NICKEL;

ALDOL REACTION; BENZYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; FUKUYAMA COUPLING REACTION; QUANTUM YIELD; REVIEW; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; ORGANIC CHEMISTRY; STEREOISOMERISM;

ASPARTIC ACID; BIOTIN; CARBON; CATALYSIS; CHEMISTRY, ORGANIC; LACTONES; LEAD; NICKEL; STEREOISOMERISM;

EID: 0038320734     PISSN: 00316903     EISSN: 13475231     Source Type: Journal    
DOI: 10.1248/yakushi.123.43     Document Type: Review

References (46)

1. du Vigneaud V., Hofmann K., Melvile D. B., Rachele J., J. Biol. Chem., 140, 763-766 (1941).
2. Mistry P. S., Dakshinamurti K., Vitam. Horm., 22, 1-55 (1964).
3. Coggeshall C. J., Heggers P. J., Robson C. M., Baker H., Ann. N. Y. Acad. Sci., 447, 389-392 (1985).
4. Maebashi M., Makino Y., Furukawa Y., Ohinata K., Kimura S., Sato T., J. Clin. Biochem. Nutr., 14, 211-218 (1993).
5. Goldberg M.W., Sternbach L. H., US Patent, 2,489,232, Nov, 22, 1949, Chem. Abstr., 45, 184b (1951).
6. Goldberg M. W., Sternbach L. H., US Patent 2489235, Nov 22, (1949) [Chem. Abstr., 45, 186a (1951)].
7. Gerecke M., Zimmermann J.-P., Ashwanden W., Helv. Chim. Acta, 53, 991-999 (1970).
8. For a review, see: Clercq P. J. D., Chem. Rev., 97, 1755-1792 (1997).
9. Seki M., Shimizu T., Inubushi K., Synthesis, 361-364 (2002).
10. Tokuyama H., Yokoshima S., Yamashita T., Fukuyama T., Tetrahedron Lett., 39, 3189-3192 (1998).
11. Shimizu T., Seki M., Tetrahedron Lett., 41, 5099-5101 (2000).
12. Shimizu T., Seki M., Tetrahedron Lett., 42, 429-432 (2001).
13. Shimizu T., Seki M., Tetrahedron Lett., 43, 1039-1042 (2002).
14. Senuma M., Fujii T., Seto M., Okamura K., Date T., Kinumaki A., Chem. Pharm. Bull., 38, 882-887 (1990).
15. Iriuchijima S., Hasegawa K., Tsuchihashi G., Agric. Biol. Chem., 46, 1907-1910 (1982).
16. Poetsch E., Casutt M., Chimia, 41, 148-150 (1987).
17. Matsuki K., Inoue H., Takeda M., Tetrahedron Lett., 34, 1167-1170 (1993).
18. Chen F. E., Huang Y.-D., Fu H., Cheng Y., Zhang D.-M., Li Y.-Y., Peng Z.-Z., Synthesis, 2004-2008 (2000).
19. Choi C., Tian S.-K., Deng L., Synthesis, 1737-1741 (2001).
20. For reviews on the utilization of aspartic acid to drug synthesis, see: Matsumoto K., Seki M., J. Syn. Org. Chem. Jpn., 49, 26-41 (1991).
21. Seki M., Matsumoto K., Bioindustry, 12, 5-19 (1995).
22. McGarvey G. J., Williams J. M., Hiner R. N., Matsubara Y., Oh T., J. Am. Chem. Soc., 108, 4943-4952 (1986).
23. Yoda H., Nakagami Y., Takabe K., Tetrahedron: Asymmetry, 5, 169-172 (1994).
24. For example, see: Seki M., Shimizu T., Matsumoto K., J. Org. Chem., 65, 1298-1304 (2000).
25. Schneider F., Liebigs Ann. Chem., 529, 1-10 (1937).
26. Hayashi K., Nunami K., Kato J., Yoneda N., Kubo M., Ochiai T., Ishida R., J. Med. Chem., 32, 289-297 (1989).
27. Isaka I., Kubo K., Takashima M., Murakami M., Yakugaku Zasshi, 88, 964-970 (1968).
28. Holick W., Pauling H., Cottong N. A., European Patent Appl. EP 0 154 225 A2, Feb. 14, (1985) [Chem. Abstr., 104, 168,273f (1986)].
29. Ohashi N., Ikeda T., Shimago K., Takahashi T., Ishizumi K., European Patent Appl. EP 84377, Jul. 27 (1983) [Chem. Abstr., 100, 34,338q (1984)].
30. Olah G. A., Narang S. C., Gupta B. G. B., Malhotra R., J. Org. Chem., 44, 1247-1251 (1979).
31. Kolb M., Barth J., Syn. Commun., 11, 763-767 (1981).
32. Lipshutz B. H., Wodd M. R., Tirado R., J. Am. Chem. Soc., 117, 6126-6127 (1995).
33. 1H NMR spectroscopy: enhancement (10%) of the signal of the C-3 hydrogen atom was observed in the compound 18 when the olefinic hydrogen was irradiated.
34. Savarin C., Srogl J., Liebeskind L. S., Org. Lett., 2, 3229-3231 (2000) and references cited therein.
35. Jackson R. F. W., Moore R. J., Dexter C. S., J. Org. Chem., 63, 7875-7884 (1998).
36. Marck G., Villiger A., Buchecker R., Tetrahedron Lett., 35, 3277-3280 (1994).
37. Ennis D. S., McManus J., Wood-Kaczmar W., Richardson J., Smith G. E., Carstairs A., Org. Proc. Res. Dev., 3, 248-252 (1999).
38. LeBlond C. R., Andrews A. T., Sun Y., Sowa J. R. Jr., Org. Lett., 3, 1555-1557 (2001).
39. Sakurai H., Tsukuda T., Hirao T., J. Org. Chem., 67, 2721-2722 (2002).
40. Heinenreich R.G., Köohler K., Krauter J. G. E., Pietsch J., Synlett, 1118-1122 (2002).
41. Roth G. P., Farina V., Tetrahedron Lett., 36, 2191-2194 (1995).
42. Liebeskind L. S., Pena-Cabrera E., Org. Synth., 77, 135-140 (1999).
43. Rossi R., Bellina F., Carpita A., Gori R., Synlett, 344-346 (1995).
44. Rosa M. A. D. L., Velarde E., Guzman A., Syn. Commun., 20, 2059-2064 (1990).
45. Bleicher L., Cosford N. D. P., Synlett, 1115-1116 (1995).
46. Deroose F. D., Clercq P. J. D., J. Org. Chem., 60, 321-330 (1995).