Total synthesis of myriocin

Tetrahedron Letters

Volumn 43, Issue 51, 2002, Pages 9361-9363

  Lee, Kee Young ^a   Oh, Chang Young ^a   Kim, Yong Hyun ^a   Joo, Jae Eun ^a   Ham, Won Hun ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; IODINE DERIVATIVE; OXAZOLINE DERIVATIVE; PALLADIUM; THERMOZYMOCIDIN; VINYL DERIVATIVE; ZINC;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0037121588     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02371-7     Document Type: Article

References (31)

1. Kluepfel D., Bagli J., Baker H., Charest M.-P., Kudelski A., Sehgal S.N., Vezina C. J. Antibiotics. 25:1972;109.
2. T-Jacques M. J. Org. Chem. 38:1973;1253.
3. Aragozzini F., Manachini P.L., Craveri R., Rindone R., Scolastico C. Tetrahedron. 13:1972;5493.
4. Destro R., Colombo A. J. Chem. Soc., Perkin Trans. 2. 1979;896.
5. Fujita T., Inoue K., Yamamoto S., Ikumoto T., Sasaki S., Toyama R., Chiba K., Hoshino Y., Okumoto T.J. Antibiotics. 47:1994;208.
6. For total synthesis of myriocin, see: (a) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Chem. Commun. 1982, 488; (b) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1983, 1613; (c) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 994; (d) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Tetrahedron 1995, 51, 6209; (e) Sano, S.; Kobayashi, Y.; kondo, T.; Takebayashi, M.; Maruyama, S.; Fuita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097; (f) Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887. For formal synthesis of myriocin, see: (g) Rao, A. V. R.; Gurjar, M. K.; Devi, T. R.; Kumar, K. R. Tetrahedron Lett. 1993, 34, 1653; (h) Deloisy, S.; Thang, T. T.; Olesker, A.; Lukacs, G. Tetrahedron Lett. 1994, 35, 4783.
7. For total synthesis of myriocin, see: (a) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Chem. Commun. 1982, 488; (b) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1983, 1613; (c) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 994; (d) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Tetrahedron 1995, 51, 6209; (e) Sano, S.; Kobayashi, Y.; kondo, T.; Takebayashi, M.; Maruyama, S.; Fuita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097; (f) Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887. For formal synthesis of myriocin, see: (g) Rao, A. V. R.; Gurjar, M. K.; Devi, T. R.; Kumar, K. R. Tetrahedron Lett. 1993, 34, 1653; (h) Deloisy, S.; Thang, T. T.; Olesker, A.; Lukacs, G. Tetrahedron Lett. 1994, 35, 4783.
8. For total synthesis of myriocin, see: (a) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Chem. Commun. 1982, 488; (b) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1983, 1613; (c) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 994; (d) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Tetrahedron 1995, 51, 6209; (e) Sano, S.; Kobayashi, Y.; kondo, T.; Takebayashi, M.; Maruyama, S.; Fuita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097; (f) Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887. For formal synthesis of myriocin, see: (g) Rao, A. V. R.; Gurjar, M. K.; Devi, T. R.; Kumar, K. R. Tetrahedron Lett. 1993, 34, 1653; (h) Deloisy, S.; Thang, T. T.; Olesker, A.; Lukacs, G. Tetrahedron Lett. 1994, 35, 4783.
9. For total synthesis of myriocin, see: (a) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Chem. Commun. 1982, 488; (b) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1983, 1613; (c) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 994; (d) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Tetrahedron 1995, 51, 6209; (e) Sano, S.; Kobayashi, Y.; kondo, T.; Takebayashi, M.; Maruyama, S.; Fuita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097; (f) Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887. For formal synthesis of myriocin, see: (g) Rao, A. V. R.; Gurjar, M. K.; Devi, T. R.; Kumar, K. R. Tetrahedron Lett. 1993, 34, 1653; (h) Deloisy, S.; Thang, T. T.; Olesker, A.; Lukacs, G. Tetrahedron Lett. 1994, 35, 4783.
10. For total synthesis of myriocin, see: (a) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Chem. Commun. 1982, 488; (b) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1983, 1613; (c) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 994; (d) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Tetrahedron 1995, 51, 6209; (e) Sano, S.; Kobayashi, Y.; kondo, T.; Takebayashi, M.; Maruyama, S.; Fuita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097; (f) Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887. For formal synthesis of myriocin, see: (g) Rao, A. V. R.; Gurjar, M. K.; Devi, T. R.; Kumar, K. R. Tetrahedron Lett. 1993, 34, 1653; (h) Deloisy, S.; Thang, T. T.; Olesker, A.; Lukacs, G. Tetrahedron Lett. 1994, 35, 4783.
11. For total synthesis of myriocin, see: (a) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Chem. Commun. 1982, 488; (b) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1983, 1613; (c) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 994; (d) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Tetrahedron 1995, 51, 6209; (e) Sano, S.; Kobayashi, Y.; kondo, T.; Takebayashi, M.; Maruyama, S.; Fuita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097; (f) Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887. For formal synthesis of myriocin, see: (g) Rao, A. V. R.; Gurjar, M. K.; Devi, T. R.; Kumar, K. R. Tetrahedron Lett. 1993, 34, 1653; (h) Deloisy, S.; Thang, T. T.; Olesker, A.; Lukacs, G. Tetrahedron Lett. 1994, 35, 4783.
12. For total synthesis of myriocin, see: (a) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Chem. Commun. 1982, 488; (b) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1983, 1613; (c) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 994; (d) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Tetrahedron 1995, 51, 6209; (e) Sano, S.; Kobayashi, Y.; kondo, T.; Takebayashi, M.; Maruyama, S.; Fuita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097; (f) Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887. For formal synthesis of myriocin, see: (g) Rao, A. V. R.; Gurjar, M. K.; Devi, T. R.; Kumar, K. R. Tetrahedron Lett. 1993, 34, 1653; (h) Deloisy, S.; Thang, T. T.; Olesker, A.; Lukacs, G. Tetrahedron Lett. 1994, 35, 4783.
13. For total synthesis of myriocin, see: (a) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Chem. Commun. 1982, 488; (b) Banfi, L.; Bretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1983, 1613; (c) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 994; (d) Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Tetrahedron 1995, 51, 6209; (e) Sano, S.; Kobayashi, Y.; kondo, T.; Takebayashi, M.; Maruyama, S.; Fuita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097; (f) Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887. For formal synthesis of myriocin, see: (g) Rao, A. V. R.; Gurjar, M. K.; Devi, T. R.; Kumar, K. R. Tetrahedron Lett. 1993, 34, 1653; (h) Deloisy, S.; Thang, T. T.; Olesker, A.; Lukacs, G. Tetrahedron Lett. 1994, 35, 4783.
14. Lee K.-Y., Kim Y.-H., Park M.-S., Ham W.-H. Tetrahedron Lett. 39:1998;8129.
15. Lee K.-Y., Kim Y.-H., Park M.-S., Oh C.-Y., Ham W.-H. J. Org. Chem. 64:1999;9450.
16. Lee K.-Y., Kim Y.-H., Oh C.-Y., Ham W.-H. Org. Lett. 2:2000;4041.
17. Dess D.B., Martin J.C. J. Org. Chem. 48:1983;4155.
18. Meyers A.G., Zhong B., Movassaghi M., Kung D.W., Lanman B.A., Kwon S. Tetrahedron Lett. 41:2000;1359.
19. Denis J.-N., Correa A., Greene A.E. J. Org. Chem. 56:1991;6939.
20. Green G., Griffith W.P., Hollinshead D.M., Ley S.V., Schroder M. J. Chem. Soc., Perkin Trans. 1. 1984;681.
21. Berkowitz D.B., Mcfadden J.M., Chisowa E., Semerad C.L. J. Am. Chem. Soc. 122:2000;11031.
22. For reviews, see: (a) Marshall, J. A. Chem. Rev. 1996, 96, 31; (b) Marshall, J. A. Chem. Rev. 2000, 100, 3163.
23. For reviews, see: (a) Marshall, J. A. Chem. Rev. 1996, 96, 31; (b) Marshall, J. A. Chem. Rev. 2000, 100, 3163.
24. 3).
25. (a) Takai K., Nitta K., Utimoto K. J. Am. Chem. Soc. 1986, 108, 7408;
26. (b) Kende A.S., DeVita R.J. Tetrahedron Lett. 1990, 31, 307;
27. (c) Evans D.A., Black W.C. J. Am. Chem. Soc. 1993, 115, 4497.
28. Preparation of alkyl iodide 13:
29. Erdik E. Tetrahedron. 48:1992;9577.
30. Negishi E., Ay M., Culevich Y.V., Noda Y. Tetrahedron Lett. 34:1993;1437.
31. Williams D.R., Kissel W.S. J. Am. Chem. Soc. 120:1998;11198.