Total synthesis of erythronolide A by MgII-mediated cycloadditions of nitrile oxides

Angewandte Chemie - International Edition

Volumn 44, Issue 26, 2005, Pages 4036-4038

  Muri, Dieter ^a   Lohse Fraefel, Nina ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Asymmetric synthesis; Cycloaddition; Erythronolides; Macrolactonization; Nitrile oxides

Indexed keywords

COMPLEXATION; ELECTRONIC STRUCTURE; MAGNESIUM PRINTING PLATES; NITRILE RESINS;

CYCLOADDITIONS; FOCAL POINTS; NITRILE OXIDES; POLYKETIDES;

SYNTHESIS (CHEMICAL);

DRUG DERIVATIVE; ERYTHROMYCIN; ERYTHRONOLIDE A; MAGNESIUM; NITRILE; OXIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CYCLIZATION; ERYTHROMYCIN; MAGNESIUM; MOLECULAR STRUCTURE; NITRILES; OXIDES;

EID: 21244451554     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500172     Document Type: Article

References (45)

1. J. M. McGuire, R. L. Bunch, R. C. Anderson, H. E. Boaz, E. H. Flynn, H. M. Powell, J. W. Smith, Antibiot. Chemother. 1952, 2, 281.
2. The first total synthesis of an erythronolide analogue was reported in 1978: E. J. Corey, E. J. Trybulski, L. S. Melvin, Jr., K. C. Nicolaou, J. A. Secrist, R. Lett, J. R. Sheldrake, D. J. Brunell, M. F. Haslanger, S. Kim, S.-e. Yoo, J. Am. Chem. Soc. 1978, 100, 4618;
3. E. J. Corey, E. J. Trybulski, L. S. Melvin, Jr., K. C. Nicolaou, J. A. Secrist, R. Lett, J. R. Sheldrake, D. J. Brunell, M. F. Haslanger, S. Kim, S.-e. Yoo, J. Am. Chem. Soc. 1978, 100, 4620.
4. For reviews on early synthetic work, see: a) I. Paterson, M. M. Mansuri, Tetrahedron 1985, 41, 3569;
5. b) J. Mulzer, Angew. Chem. 1991, 103;
6. Angew. Chem. Int. Ed. Engl. 1991, 30, 1452.
7. For recent studies on the syntheses of erythromycins and erythronolides, see: a) R. Stürmer, K. Ritter, R. W. Hoffmann, Angew. Chem. 1993, 105, 112;
8. Angew. Chem. Int. Ed. Engl. 1993, 32, 101;
9. b) S. F. Martin, T. Hida, P. R. Kym, M. Loft, A. Hodgson, J. Am. Chem. Soc. 1997, 119, 3193;
10. c) D. A. Evans, A. S. Kim, R. Metternich, V. J. Novack, J. Am. Chem. Soc. 1998, 120, 5921;
11. d) P. J. Hergenrother, A. Hodgson, A. S. Judd, W.-C. Lee, S. F. Martin, Angew. Chem. 2003, 115, 3400;
12. Angew. Chem. Int. Ed. 2003, 3278;
13. e) Z.-H. Peng, K. A. Woerpel, J. Am. Chem. Soc. 2003, 125, 6018.
14. a) J. W. Bode, N. Fraefel, D. Muri, E. M. Carreira, Angew. Chem. 2001, 113, 2128;
15. Angew. Chem. Int. Ed. 2001, 40, 2082;
16. b) for comprehensive reviews on cycloadditions of nitrile oxides, see: P. Caramella, P. Grünanger in 1,3-Dipolar Cycloaddition Chemistry, Vol. 1 (Ed.: A. Padwa), Wiley-Interscience, New York, 1984, pp. 292-392;
17. C. J. Easton, C. M. M. Hughes, G. P. Savage, G. W. Simpson, Adv. Heterocycl. Chem. 1994, 60, 261;
18. c) for applications of cycloadditions of nitrile oxides in the synthesis of heterocycles and natural products, see: "Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products" by V. Jäger, P. A. Colinas in The Chemistry of Heterocydic Compounds, Vol. 59 (Eds.: A. Padwa, W. H. Pearson), Wiley, New York, 2002, pp. 361-472.
19. Oxime 2 was prepared in three steps from (S)-methyl-3-hydroxyisobutyrate, which is available for less than 1 € per gram from Mitsubishi Rayon Co., Ltd. We would like to thank Mitsubishi Rayon Co. for a generous gift of (S)-methyl-3-hydroxyisobutyrate.
20. a) Several preparations of chiral olefin 3 have been reported; for our purposes it was prepared from enantiomerically pure 2-hydroxy-3-pentyne, itself prepared by the method of R. Noyori, J. Am. Chem. Soc. 1997, 119, 8738;
21. b) for another procedure, see: O. Hamed, P. M. Henry, Organometallics 1997, 16, 4903.
22. W. P Griffith, S. V. Ley, G. P. Whitecomb, A. D. White, J. Chem. Soc. Chem. Commun. 1987, 1625.
23. 2; the bromide is available in three steps from (S)-methyl-3-hydroxyisobutyrate: P. M. Smith, E. J. Thomas, J. Chem. Soc. Perkin Trans. 1 1998, 3541.
24. a) D. P. Curran, J. Am. Chem. Soc. 1983, 105, 5826;
25. b) D. P. Curran, S. A. Scanga, C. J. Fenk, J. Org. Chem. 1984, 49, 3474.
26. a) Y. Ito, M. Yamaguchi, Tetrahedron Lett. 1983, 24, 5385;
27. b) T. Nakata, Y. Tani, M. Hatozaki, T. Oishi, Chem. Pharm. Bull. 1984, 32, 1411;
28. c) D. A. Evans, M. D. Ennis, and T. Le, N. Mandel, G. Mandel, J. Am. Chem. Soc. 1984, 106, 1154.
29. G. Wittig, U. Schöllkopf, Chem. Ber. 1954, 87, 1318.
30. Substrate-directed dihydroxylation on a similar system proved troublesome; no diastereoselectivity was observed but the yield was excellent: S. D. Burke, F. J. Schoenen, M. S. Nair, Tetrahedron Lett. 1987, 28, 4143.
31. For recent reviews on Sharpless asymmetric dihydroxylations, see: a) H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483;
32. b) R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 2000, pp. 357.
33. On a similar system, selective deprotection of the tertiary hydroxy group was observed under acidic conditions (dichloroacetic acid, MeOH, 0°C).
34. Woodward's early investigation revealed a 9-(S)-hydroxy group, protected as a cyclic acetal, ideal for a successful lactonization of the carboxylic acid: a) R. B. Woodward, E. Logusch, K. P. Nambiar, K. Sakan, D. E. Ward, B.-W. Au-Yeung, P. Balaram, L. J. Browne, P. J. Card, C. H. Chen, R. B. Chênevert, A. Fliri, K. Frobel, H.-J. Gais, D. G. Garratt, K. Hayakawa, W. Heggie, D. P. Hesson, D. Hoppe, I. Hoppe, J. A. Hyatt, D. Ikeda, P. A. Jacobi, K. S. Kim, Y. Kobuke, K. Kojima, K. Krowicki, V. J. Lee, T. Leutert, S. Malchenko, J. Martens, R. S. Matthews, B. S. Ong, J. B. Press, T. V. Rajan Babu, G. Rousseau, H. M. Sauter, M. Suzuki, K. Tatsuta, L. M. Tolbert, E. A. Truesdale, I. Uchida, Y. Ueda, T. Uyehara, A. T. Vasella, W. C. Vladechick, P. A. Wade, R. M. Williams, H. N.-C. Wong, J. Am. Chem. Soc. 1981, 103, 3210;
35. b) R. B. Woodward, E. Logusch, K. P. Nambiar, K. Sakan, D. E. Ward, B.-W. Au-Yeung, P. Balaram, L. J. Browne, P. J. Card, C. H. Chen, R. B. Chênevert, A. Fliri, K. Frobel, H.-J. Gais, D. G. Garratt, K. Hayakawa, W. Heggie, D. P. Hesson, D. Hoppe, I. Hoppe, J. A. Hyatt, D. Ikeda, P. A. Jacobi, K. S. Kim, Y. Kobuke, K. Kojima, K. Krowicki, V. J. Lee, T. Leutert, S. Malchenko, J. Martens, R. S. Matthews, B. S. Ong, J. B. Press, T. V. Rajan Babu, G. Rousseau, H. M. Sauter, M. Suzuki, K. Tatsuta, L. M. Tolbert, E. A. Truesdale, I. Uchida, Y. Ueda, T. Uyehara, A. T. Vasella, W. C. Vladechick, P. A. Wade, R. M. Williams, H. N.-C. Wong, J. Am. Chem. Soc. 1981, 103, 3213;
36. R. B. Woodward, E. Logusch, K. P. Nambiar, K. Sakan, D. E. Ward, B.-W. Au-Yeung, P. Balaram, L. J. Browne, P. J. Card, C. H. Chen, R. B. Chênevert, A. Fliri, K. Frobel, H.-J. Gais, D. G. Garratt, K. Hayakawa, W. Heggie, D. P. Hesson, D. Hoppe, I. Hoppe, J. A. Hyatt, D. Ikeda, P. A. Jacobi, K. S. Kim, Y. Kobuke, K. Kojima, K. Krowicki, V. J. Lee, T. Leutert, S. Malchenko, J. Martens, R. S. Matthews, B. S. Ong, J. B. Press, T. V. Rajan Babu, G. Rousseau, H. M. Sauter, M. Suzuki, K. Tatsuta, L. M. Tolbert, E. A. Truesdale, I. Uchida, Y. Ueda, T. Uyehara, A. T. Vasella, W. C. Vladechick, P. A. Wade, R. M. Williams, H. N.-C. Wong, J. Am. Chem. Soc. 1981, 103, 3215.
37. a) J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989;
38. studies in the context of erythronolide macrolactoniziation: Y. Sakurai, M. Hikota, K. Horita, O. Yonemitsu, Chem. Pharm. Bull. 1992, 40, 2540.
39. a) Formation of erythromycin A oxime, see: A. M. Costa, J. Vilarrasa, Tetrahedron Lett. 2000, 41, 3371;
40. b) Glycoside cleavage, see: R. A. LeMahieu, M. Carson, R. W. Kirstead, J. Antibiot. 1975, 28, 704;
41. Regeneration of the ketone, see: R. A. LeMahieu, M. Carson, R. W. Kierstead, L. M. Fern, J. Med. Chem. 1974, 17, 953.
42. For recent modifications, see, for example: a) Y. Watanabe, T. Adachi, T. Asaka, M. Kashimura, S. Morimoto, Heterocycles 1990, 31, 2121;
43. b) R. L. Elliott, D. Pireh, G. Griesgraber, A. M. Nilius, P. J. Ewing, M. H. Bui, P. M. Raney, R. K. Flamm, K. Kim, R. F. Henry, D. T. W. Chu, J. J. Plattner, Y. S. Or, J. Med. Chem. 1998, 41, 1651;
44. c) T. Tanikawa, T. Asaka, M. Kashimura, K. Suzuki, H. Sugiyama, M. Sato, K. Kameo, S. Morimoto, A. Nishida, J. Med. Chem. 2003, 46, 2706;
45. d) M. C. Hsu, A. J. Junia, A. R. Haight, W. Zhang, J. Org. Chem. 2004, 69, 3907.