Stereoselective synthesis of erythronolide A via nitrile oxide cycloadditions and related studies

Journal of Organic Chemistry

Volumn 74, Issue 22, 2009, Pages 8695-8712

  Muri, Dieter ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC DIHYDROXYLATION; CHEMICAL EQUATIONS; CYCLOADDITIONS; GRIGNARD REACTION; NITRILE OXIDES; STEREOSELECTIVE SYNTHESIS;

CYANIDES; MAGNESIUM; NITROGEN OXIDES; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

ERYTHRONOLIDE A; NITRILE OXIDE;

ARTICLE; CHELATION; CYCLOADDITION; DIHYDROXYLATION; DRUG SYNTHESIS; GRIGNARD REACTION; STEREOCHEMISTRY; SYNTHESIS;

CYCLIZATION; ERYTHROMYCIN; MOLECULAR CONFORMATION; NITRILES; OXIDES; STEREOISOMERISM;

EID: 70449672738     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901817b     Document Type: Article

References (78)

1. Mc Guire, M.; Bunch, R. L.; Anderson, R. C.; Boaz, H. E.; Flynn, E. H.; Powell, H. M.; Smith, J. W. Antibiot. Chemother. 1952, 2, 281-283.
2. For reviews on early synthetic work, see: Paterson, I; Mansuri, M. M. Tetrahedron 1985, 41, 3569-3624.
3. Mulzer, J. Angew. Chem. 1991, 103,
4. Angew. Chem., Int. Ed. Engl. 1991, 30, 1452-1454.
5. For recent studies on the syntheses of erythromycins and erythronolides, see: (a) Stürmer, R.; Ritter, K.; Hoffmann, R.W. Angew. Chem. 1993, 105, 112;
6. Angew. Chem., Int. Ed. Engl. 1993, 32, 101.
7. (b) Martin, S. F.; Hida, T.; Kym, P. R.; Loft, M.; Hodgson, A. J. Am. Chem. Soc. 1997, 119, 3193.
8. (c) Evans, D. A.; Kim, A. S.; Metternich, R.; Novack, V. J. J. Am. Chem. Soc. 1998, 120, 5921.
9. (d) Hergenrother, P. J.; Hodgson, A.; Judd, A. S.; Lee, W.-C.; Martin, S. F. Angew. Chem. 2003, 115, 3400;
10. Angew. Chem., Int. Ed., 2003, 3278.
11. (e) Peng, Z.-H.; Woerpel, K. A. J. Am. Chem. Soc. 2003, 125, 6018.
12. Woodward, R. B. In Perspectives in Organic Synthesis; Todd, A., Ed.; Interscience Publishers: New York, 1956; p 155 (see p 160).
13. Corey, E. J.; Trybulski, E. J.; Melvin, L. S. Jr.; Nicolaou, K. C.; Secrist, J. A.; Lett, R.; Sheldrake, J. R.; Brunell, D. J.; Haslanger, M. F.; Kim, S.; Yoo, S.-e. J. Am. Chem. Soc. 1978, 100, 4618-4620.
14. Corey, E. J.; Kim, S.; Yoo, S.-e.; Nicolaou, K. C.; Lawrence, S. M. Jr; Brunelle, D. J.; Falck, J. R.; Trybulski, E. J.; Lett, R.; Sheldrake, P. W. J. Am. Chem. Soc. 1978, 100, 4620-4622.
15. Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E.; Au-Yeung, B.-W.; Balaram, P.; Browne, L. J.; Card, P. J.; Chen, C. H.; Chênevert, B.; Fliri, A.; Frobel, K.; Gais, H.-J.; Garratt, D. G.; Hayakawa, K.; Heggie, W.; Hesson, S. P.; Hoppe, D.; Hoppe, I.; Hyatt, J. A.; Ikeda, D.; Jacobi, P. A.; Kim, K. S.; Kobuke, Y.; Kojima, K.; Krowicki, K.; Lee, V. J.; Leutert, T.; Malchenko, S.; Martens, J.; Mathews, R. S.; Ong, B. S.; Press, J. B.; Rajan Babu, T. V.; Rousseau, B.; Sauter, H. M.; Suzuki, M.; Tatsuta, K.; Tolbert, L. M.; Truesdale, E. A.; Uchida, I.; Ueda, Y.; Uyehara, T.; Vasella, A. T.; Vladuchick, W. C.; Wade, P. A.; Williams, R. M.; Wong, N.-C. J. Am. Chem. Soc. 1981, 103, 3210-3213; 3213-3215; 3215-3217.
16. Toshima, K.; Nozaki, Y.; Mukaiyama, S.; Tamai, T.; Nakata, M.; Tatsuta, K.; Kinoshita, M. J. Am. Chem. Soc. 1995, 117, 3717-3727.
17. (a) Kanemasa, S.; Kobayashi, S.; Nishiuchi, M.; Yamamoto, H.; Wasa, E. Tetrahedron Lett. 1991, 32, 6367-6370.
18. (b) Kanemasa, S.; Nishiushi, M.; Wada, E. Tetrahedron Lett. 1992, 33, 1357-1360.
19. (c) Kanemasa, S.; Nishiuchi, M.; Kamimura, A.; Hori, K. J. Am. Chem. Soc. 1994, 116, 2324-2339.
20. For previous investigations from our laboratory involving nitrile oxide cycloadditions with allylic alcohols, see: (a) Bode, J. W.; Fraefel, N.; Muri, D.; Carreira, E. M. Angew. Chem., Int. Ed. 2001, 40, 2082.
21. (b) Bode, J. W.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 3611.
22. (c) Bode, J. W.; Carreira, E. M. J. Org. Chem. 2001, 66, 6410.
23. (d) Fader, L. D.; Carreira, E. M. Org. Lett. 2004, 14, 2485.
24. (e) Muri, D.; Lohse-Fraefel, N.; Carreira, E. M. Angew. Chem., Int. Ed. 2005, 44, 4036.
25. (f) Lohse-Fraefel, N.; Carreira, E. M. Org. Lett. 2005, 7, 2011.
26. (g) Becker, N.; Carreira, E. M. Org. Lett. 2007, 9, 3857.
27. (h) Szpilman, A. M.; Cereghetti, D. M.; Wurtz, N. R.; Manthorpe, J. M.; Carreira, E. M. Angew. Chem. 2008, 47, 4335.
28. (i) Szpilman, A. M.; Manthorpe, J. M.; Carreira, E. M. Angew. Chem. 2008, 47, 4339.
29. (j) Kleinbeck, F.; Carreira, E. M. Angew. Chem., Int. Ed. 2009, 48, 578.
30. Direct reduction to the aldehyde was suitable up to 5 g. On a larger scale, complete reduction to the alcohol and reoxidation to the aldehyde under Ley's condition gave better results.
31. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666.
32. (a) Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285-287.
33. (b) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739.
34. Hamed, O.; Henry, P. M. Organometallics 1997, 16, 4903-4909.
35. Lindlar, H. Helv. Chim. Acta 1952, 35, 446.
36. Mintz, M. J.; Walling, C. Org. Synth. 1969, 49, 9-12.
37. The bromide 167 was already prepared earlier: Meyer, S. D.; Miwa, T.; Nakatsuka, M.; Schreiber, S. L. J. Org. Chem. 1992, 57, 5058-5060.
38. For an example of a lithium-halogen exchange and subsequent transmetallation with MgBr2, see: Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 5583-5601.
39. (a) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559-2562.
40. (b) For a review on the use of stable nitroxyl radicals for the oxidation of alcohols, see: de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153-1174.
41. For excellent reviews, see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
42. (b) Johnson, R. A.; Sharpless, K. B. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, J., Ed.; Wiley-VCH: New York, 2000; pp 357-398.
43. For an excellent review on selective deprotection of silyl ethers, see: Nelson, T. D.; Crouch, R. D. Synthesis 1996, 1031-1069.
44. (a) With zirconocene complexes: Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Syntheses 1986, 774-776.
45. (b) TEMPO/sodium bromite: Inokuchi, T.; Matsumoto, S.; Nishiyama, T.; Torii, S. J. Org. Chem. 1990, 55, 462-466.
46. (c) TEMPO/trichloroiso-cyanuric acid: De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041-3043.
47. (d) TEMPO/peroxodisulfate/ silver nitrate: Kochkar, H.; Lassalle, L.; Morawietz, M.;Hölderich, W. F. J. Catal. 2000, 194, 343-351.
48. (e) TEMPO/NCS: Einhorn, J.; Einhorn, C.; Ratajczak, R.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452-7454.
49. (f) TEMPO/ NaOBr: Chan, P. S.; Robyt, J. F. J. Carbohydr. Chem. 1996, 15, 819-830.
50. De Luca, L.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2001, 66, 7907-7909.
51. Hutchinson, D. K.; Fuchs, P. L. J. Am. Chem. Soc. 1987, 109, 4755-4756.
52. Corey, E. J.; Kim, C. U. J. Am. Chem. Soc. 1972, 94, 7586-7587.
53. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 5, 399-402.
54. Bowden, K.; Heilbron, I. M.; Jones, E. R. H.; Weedon, B. C. L. J. Chem. Soc. 1946, 39-45.
55. Mazitschek, R.; Mülbaier, M.; Giannis, A. Angew. Chem., Int. Ed. 2002, 41, 4059-4061.
56. De Mico, A.; Margarita, R.; Parlanti, L.; Vescovi, A.; Piancatelli, G. J. Org. Chem. 1997, 62, 6974-6977.
57. Mancuso, A. J.; Swern, D. Synthesis 1981, 165-185.
58. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
59. Lindgren, B. O.; Nilsson, T. Acta Chem. Scand. 1973, 27, 888-890.
60. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
61. Curran, D. P.; Zhang, J. J. Chem. Soc., Perkin Trans. 1 1991, 2613-2625.
62. Curran, D. P. J. Am. Chem. Soc. 1983, 105, 5826-5833.
63. Souza, F. E. S.; Rodrigo, R. Chem. Commun. 1999, 1947-1948.
64. Kim, B. H.; Jacobs, P. B.; Elliott, R. L.; Curran, D. P. Tetrahedron 1988, 44, 3079-3092.
65. Bode, J. W.; Carreira, E. M. Org. Lett. 2001, 3, 1587-1590.
66. Baraldi, P. G.; Barco, A.; Benetti, S.; Manfredini, S.; Simoni, D. Synthesis 1987, 276-278.
67. Ito, Y.; Yamaguchi, M. Tetrahedron Lett. 1983, 24, 5385-5386.
68. Chen, K.-M.; Gunderson, K. G.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Chem. Lett. 1987, 16, 1923-1926.
69. Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012.
70. Bode, J. W. Ph.D. thesis, Diss. ETH No. 14115, 2001, ETH, Zürich.
71. (a) Kinoshita, M.; Arai, M.; Ohsawa, N.; Nakata, M. Tetrahedron Lett. 1986, 27, 1815-1818.
72. (b) Bull. Chem. Soc. Jpn. 1989, 62, 2618-2635.
73. Corey already described the acid sensitivity of erythronolide A and the subsequent formation of a tricyclic ketal: Schomburg, D.; Hopkins, P. B.; Lipscomb, W. N; Corey, E. J. J. Org. Chem. 1980, 43, 1544-1546.
74. This aldehyde was described earlier: Gaucher, A.; Ollivier, J.; Marguerite, J.; Paugam, R.; Salaün, J. Can. J. Chem. 1994, 72, 1312-1327
75. Hamed, O.; Henry, P. M. Organometallics 1997, 16, 4903-4909.
76. Walkup, R. D.; Kahl, J. D.; Kane, R. K. J. Org. Chem. 1998, 63, 9113-9116.
77. Organ, M. G.; Wang, J. J. Org. Chem. 2003, 68, 5568-5574.
78. Smith, P. M.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1998, 3541-3556.