Stereoselective synthesis of pamamycin-607

Journal of the American Chemical Society

Volumn 124, Issue 49, 2002, Pages 14655-14662

  Jeong, Eun Jeong ^a   Kang, Eun Joo ^a   Sung, Lee Taek ^a   Hong, Sung Kil ^a   Lee, Eun ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

RADICAL CYCLIZATION;

KETONES; ORGANIC ACIDS; SUBSTRATES; SYNTHESIS (CHEMICAL);

ANTIBIOTICS;

MACROLIDE; PAMAMYCIN 607; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CYCLIZATION; DEPROTECTION REACTION; DRUG SYNTHESIS; OXIDATION; RADICAL REACTION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTIFUNGAL; MACROLIDES; ORGANIC CHEMICALS; STEREOISOMERISM; STREPTOMYCES;

EID: 0037065296     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0279646     Document Type: Article

References (61)

1. McCann, P. A.; Pogell, B. M. J. Antibiot. 1979, 32, 673-678.
2. Kondo, S.; Yasui, K.; Katayama, M.; Marumo, S.; Kondo, T.; Hattori, H. Tetrahedron Lett. 1987, 28, 5861-5864.
3. (a) Kondo, S.; Yasui, K.; Natsume, M.; Katayama, M.; Marumo, S. J. Antibiot. 1988, 41, 1196-1204.
4. (b) Natsume, M.; Kondo, S.; Marumo, S. J. Chem. Soc. Chem. Comm. 1989, 1911-1913.
5. (c) Natsume, M.; Yasui, K.; Kondo, S.; Marumo, S. Tetrahedron Lett. 1991, 32, 3087-3090.
6. (d) Natsume, M.; Tazawa, J.; Yagi, K.; Abe, H.; Kondo, S.; Marumo, S. J. Antibiot. 1995, 48, 1159-1164.
7. (e) Natsume, M.; Honda, A.; Oshima, Y.; Abe, H.; Kondo, S.; Tanaka, F.; Marumo, S. Biosci. Biotech. Biochem. 1995, 59, 1766-1768.
8. (a) Stengel, C.; Reinhardt, G.; Gräfe, U. J. Basic Microbiol. 1992, 32, 339-345.
9. (b) Gräfe, U.; Stengel, C.; Möllmann, U.; Heinisch, L. Pharmazie 1994, 49, 343-346.
10. (c) Grigoriev, P.; Berg, A.; Schlegel, R.; Gräfe, U. Bioelectrochem. Bioenerg. 1996, 39, 295-298.
11. (d) Härtl, A.; Stelzner, A.; Schlegel, R.; Heinze, S.; Hülsmann, H.; Fleck, W.; Gräfe, U. J. Antibiot. 1998, 51, 1040-1046.
12. (e) Kozone, I.; Chikamoto, N.; Abe, H.; Natsume, M. J. Antibiot. 1999, 52, 329-331.
13. (f) Pogell, B. M. Cell. Mol. Biol. 1998, 44, 461-463.
14. A total synthesis of pamamycin-607 was communicated by Professor Sung Ho Kang (Korea Advanced Institute of Science and Technology) at the CMDS Symposium 2000, Nov. 9, 2000, Daejon, Korea. A preliminary report on the total synthesis was communicated by us: (a) Lee, E.; Jeong, E. J.; Kang, E. J.; Sung, L. T.; Hong, S. K. J. Am. Chem. Soc. 2001, 123, 10 131-10 132. One paper appeared in the literature before publication of our communication and a second one appeared after publication of ours: (b) Germay, O.; Kumar, N.; Thomas, E. J. Tetrahedron Lett. 2001, 42, 4969-4974 (c) Wang, Y.; Bernsmann, H.; Gruner, M.; Metz, P. Tetrahedron Lett. 2001, 42, 7801-7804.
15. A total synthesis of pamamycin-607 was communicated by Professor Sung Ho Kang (Korea Advanced Institute of Science and Technology) at the CMDS Symposium 2000, Nov. 9, 2000, Daejon, Korea. A preliminary report on the total synthesis was communicated by us: (a) Lee, E.; Jeong, E. J.; Kang, E. J.; Sung, L. T.; Hong, S. K. J. Am. Chem. Soc. 2001, 123, 10 131-10 132. One paper appeared in the literature before publication of our communication and a second one appeared after publication of ours: (b) Germay, O.; Kumar, N.; Thomas, E. J. Tetrahedron Lett. 2001, 42, 4969-4974 (c) Wang, Y.; Bernsmann, H.; Gruner, M.; Metz, P. Tetrahedron Lett. 2001, 42, 7801-7804.
16. A total synthesis of pamamycin-607 was communicated by Professor Sung Ho Kang (Korea Advanced Institute of Science and Technology) at the CMDS Symposium 2000, Nov. 9, 2000, Daejon, Korea. A preliminary report on the total synthesis was communicated by us: (a) Lee, E.; Jeong, E. J.; Kang, E. J.; Sung, L. T.; Hong, S. K. J. Am. Chem. Soc. 2001, 123, 10 131-10 132. One paper appeared in the literature before publication of our communication and a second one appeared after publication of ours: (b) Germay, O.; Kumar, N.; Thomas, E. J. Tetrahedron Lett. 2001, 42, 4969-4974 (c) Wang, Y.; Bernsmann, H.; Gruner, M.; Metz, P. Tetrahedron Lett. 2001, 42, 7801-7804.
17. (a) Walkup, R. D.; Park, G. Tetrahedron Lett. 1988, 29, 5505-5508.
18. (b) Walkup, R. D.; Kim, S. W.; Wagy, S. D. J. Org. Chem. 1993, 58, 6486-6490.
19. (c) Walkup, R. D.; Kim, S. W. J. Org. Chem. 1994, 59, 3433-3441.
20. (d) Walkup, R. D.; Kim, Y. S. Tetrahedron Lett. 1995, 36, 3091-3094.
21. Mavropoulos, L.; Perlmutter, P. Tetrahedron Lett. 1996, 37. 3751-3754.
22. Arista, L.; Gruttadauria, M.; Thomas, E. J. Synlett 1997, 627-628.
23. (a) Mandville, G.; Girad, C.; Block, R. Tetrahedron Asymmetry 1997, 8, 3665-3673.
24. (b) Mandville, G.; Block, R. Eur. J. Org. Chem. 1999, 2303-2307.
25. (a) Solladié, G.; Salom-Roig, X. J.; Hanquet, G. Tetrahedron Lett. 2000, 41, 551-554.
26. (b) Solladié, G.; Salom-Roig, X. J.; Hanquet, G. Tetrahedron Lett. 2000, 41, 2737-2740.
27. Calter, M. A.; Bi, F. C. Org. Lett. 2000, 2, 1529-1531.
28. (a) Bernsmann, H.; Hungerhoff, B.; Fechner, R.; Fröhlich, R.; Metz, P. Tetrahedron Lett. 2000, 41, 1721-1724.
29. (b) Bernsmann, H.; Fröhlich, R.; Metz, P. Tetrahedron Lett. 2000, 41, 4347-4351.
30. (c) Bernsmann, H.; Gruner, M.; Metz, P. Tetrahedron Lett. 2000, 41, 7629-7633.
31. Kang, S. H.; Jeong, J. W. Tetrahedron Lett. 2002. 43, 3613-1616.
32. (a) Lee, E.; Tae, J. S.; Lee, C.; Park, C. M. Tetrahedron Lett. 1993, 34, 4831-4834.
33. (b) Lee, E.; Tae, J. S.; Chong, Y. H.; Park, Y. C.; Yun, M.; Kim, S. Tetrahedron Lett. 1994, 35, 129-132.
34. (c) Lee, E.; Park, C. M. J. Chem. Soc. Chem. Commun. 1994, 293-294.
35. (d) Lee, E.; Jeong, J.-w.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765-7768.
36. (e) Lee, E.; Song, H. Y.; Kim, H. J. J. Chem. Soc., Perkin 1 1999, 3395-3396.
37. (f) Lee, E.; Kim, H. J.; Kang, E. J.; Lee, I. S.; Chung, Y. K. Chirality, 2000, 12, 360-361.
38. Lee, E. In Radicals in Organic Synthesis, Vol. 2: Applications; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim. 2001; pp 303-333.
39. Lee, E.; Park, C. M.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017-8018.
40. Lee, E.; Yoo, S.-K.; Cho, Y.-S.; Cheon, H.-S.; Chong, Y. H. Tetrahedron Lett. 1997, 38, 7757-7758.
41. Lee, E.; Yoo, S.-K.; Choo, H.; Song, H. Y. Tetrahedron Lett. 1998, 39, 317-318.
42. (a) Guindon, Y.; Lavallée, J.-F.; Boisvert, L.; Chabot, C.; Delorme, D.; Yoakim, C.; Hall, D.; Lemieux, R.; Simoneau, B. Tetrahedron Lett. 1991, 32, 27-30.
43. (b) Durkin, K.; Liotta, D.; Rancourt, J.; Lavallée, J.-F.; Boisvert, L.; Guindon, Y. J. Am. Chem. Soc. 1992, 114, 4912-4914.
44. Lee, E.; Choi, S. J. Org. Lett. 1999, 1, 1127-1128.
45. For an example of asymmetric aldol reactions, see: Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001-7031.
46. Evans, D. A.; Trotter, B. W.; Câté, B.; Colman, P. J.; Dias, L. C.; Tyler, A. N. Angew. Chem., Int. Ed. Engl. 1997, 36, 2744-2748.
47. For an example of radical cyclizations of β-aminovinyl ketones, see: Lee, E.; Kang, T. S.; Chung, C. K. Bull. Kor. Chem. Soc. 1996, 17, 212-214.
48. Arco, M. J.; Trammell, M. H.; White, J. D. J. Org. Chem. 1976, 41, 2075-2083.
49. (a) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693-2698.
50. (b) Keck, G. E.; Wager, C. A. Org. Lett. 2000, 2, 2307-2309.
51. (c) Keck, G. E.; Wager, C. A.; Sell, T.; Wager, T. T. J. Org. Chem. 1999, 64, 2172-2173.
52. Keck, G. E.; Abbott, D. E. Tetrahedron Lett. 1984, 25, 1883- 1886.
53. For examples of determination of absolute stereochemistry via O-acetyl -mandelate esters. see: Lee, E.; Lee, Y. R.; Moon, B.; Kwon, O.; Shim, M. S.; Yun, J. S. J. Org, Chem. 1994, 59, 1444-1456.
54. Somers, P. K.; Wandless, T. J.; Schreiber, S. L. J. Am. Chem. Soc. 1991, 113, 8045-8056.
55. (a) Narasaka, K.; Ukaji, Y.; Yamazaki, S. Bull. Chem. Soc. Jpn. 1986, 59. 525-533.
56. (b) Haddad, M.; Dorbais, J.; Larchevêque, M. Tetrahedron Lett. 1997, 38, 5981-5984.
57. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
58. Brouillette, W. J.; Saeed, A.; Abuelyaman, A.; Hutchison, T. L.; Wolkowicz, P. E.; McMillin, J. B. J. Org. Chem. 1994, 59, 4297-4303.
59. Takano, S.; Sugihara, T.; Satoh, S.; Ogasawara, K. J. Am. Chem. Soc. 1988, 110, 6467-6471.
60. Burke, S. D.; Zhao, Q. J. Org. Chem. 2000, 65, 1489-1500.
61. Kageyama, M.; Tamura, T.; Nantz, M. H.; Roberts, J. C.; Somfai, P.; Whritenour, D. C.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7407-7408.