A total synthesis of FK-5061

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 6856-6872

  Ireland, Robert E ^a   Gleason, James L ^a   Gegnas, Laura D ^a   Highsmith, Thomas K ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TACROLIMUS;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029806490     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951646q     Document Type: Article

References (46)

1. No reprints of this paper are available.
2. Tanaka, H.; Kuroda, A.; Marusawa, H.; Hatanaka, H.; Kino, T.; Goto, T.; Hashimoto, M.; Taga, T. J. Am. Chem. Soc. 1987, 109, 5031-5033.
3. (a) Kino, T.; Hatanaka, H.; Hashimoto, M.; Nishiyama, M.; Goto, T.; Okuhara, M.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1987, 15, 1249-1255.
4. (b) Kino, T.; Hatanaka, H.; Miyata, S.; Inamura, N.; Nishiyama, M.; Yajima, T.; Goto, T.; Okuhara, M.; Kohsaka, M.; Aoki, H.; Ochiai, T. J. Antibiot. 1987, 40, 1256-1265.
5. (a) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157-1159.
6. (b) Jones, T. K.; Reamer, R. A.; Desmond, R.; Mills, S. G. J. Am. Chem. Soc. 1990, 112, 2998-3017.
7. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 5583-5601.
8. Jones, A. B.; Villalobos, A.; Linde, R. G.; Danishefsky, S. J. J. Org. Chem. 1990, 55, 2786-2797.
9. Gu, R. L.; Sih, C. J. Tetrahedron Lett. 1990, 31, 3287-3290.
10. Smith, A. B., III; Chen, K.; Robinson, D. J.; Laakso, L. M.; Hale, K. J. Tetrahedron Lett. 1994, 35, 4271-4274.
11. FK-506 (1) numbering is used for all intermediates throughout this article.
12. Ireland, R. E.; Highsmith, T. K.; Gegnas, L. D.; Gleason, J. L. J. Org. Chem. 1992, 57, 5071-5073.
13. (a) Ireland, R. E.; Wipf, P.; Miltz, W.; Vanasse, B. J. J. Org. Chem. 1990, 55, 1423-1424.
14. (b) Ireland, R. E.; Wipf, P.; Roper, T. D. J. Org. Chem. 1990, 55, 2284-2285.
15. The use of triethylamine as the coordinating solvent moderates the reactivity of the Grignard reagent, preventing reduction of the product ketone. For preparation of Grignard reagents in triethylamine, see Ashby, E. C.; Walker, F. W. J. Org. Chem. 1968, 33, 3821-3828.
16. Ireland, R. E.; Marshall, J. A. J. Org. Chem., 1962, 27, 1620-1627.
17. Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570-1576.
18. 13C NMR analysis of a C24, C26 acetonide. Ultimate stereochemical proof arises from the X-ray structure of diol 17 and final conversion of these substrates into FK-506 (vide infra).
19. DeShong, P.; Waltermire, R. E.; Ammon, H. L. J. Am. Chem. Soc. 1988, 110, 1901-1910.
20. Coordinates and unit cell parameters for diol 17 have been deposited in the Cambridge Crystallographic Data Base. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
21. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
22. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
23. Nakata, T.; Tani, Y.; Hatozaki, M.; Oishi, T. Chem Pharm. Bull. 1984, 32, 1411-1415.
24. 10 should be inverted at C26.
25. Johnson, R. L.; Rajakumar, G.; Yu, K.; Mishra, R. K. J. Med. Chem. 1986, 29, 2104-2106.
26. Ireland, R. E.; Wipf, P. Tetrahedron Lett. 1989, 30, 919-923.
27. Gleason, J. L. Ph.D. Dissertation, University of Virginia (1994).
28. For similar Grignard additions see: (a) Somers, P. K.; Wandless, T. J.; Schreiber, S. L. J. Am. Chem. Soc. 1991, 113, 8045. (b) Rao. A. V. R.; Chakraborty, T. K.; Reddy, K. L. Tetrahedron Lett. 1991, 32, 1251-1254.
29. For similar Grignard additions see: (a) Somers, P. K.; Wandless, T. J.; Schreiber, S. L. J. Am. Chem. Soc. 1991, 113, 8045. (b) Rao. A. V. R.; Chakraborty, T. K.; Reddy, K. L. Tetrahedron Lett. 1991, 32, 1251-1254.
30. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
31. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
32. Coordinates and unit cell parameters for diol 39 have been deposited in the Cambridge Crystallographic Data Base. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
33. (a) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426.
34. (b) Wipf, P.; Smitrovich, J.; Moon, C. J. Org. Chem. 1992 57, 3178-3186.
35. Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. Tetrahedron 1984, 40, 5005-5038.
36. Corey, E. J.; Beames, D. J. J. Am. Chem. Soc. 1972, 94, 7210-7211.
37. Coleman, R. S.; Danishefsky, S. J. Heterocycles 1989, 28, 157-161.
38. Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R. J. Org. Chem. 1993, 58, 832-839.
39. Anelli, P. L.; Biffi, C.; Montanarie, F.; Quici, S. J. Org. Chem. 1987, 2559-2562.
40. King, C.; Ozog, F. J. J. Org. Chem. 1955, 20, 448-454.
41. Ireland, R. E.; Wipf, P.; Armstrong, J. D. J. Org. Chem. 1991, 56, 650-657.
42. Furstner, A.; Weidmann, H. J. Org. Chem. 1989, 54, 2307-2311.
43. Ireland, R. E.; Liu, L.-B.; Roper, T. D.; Gleason, J. L. Manuscript in preparation.
44. The difference in reactivity in these two systems is unclear. The enediol systems studied in model systems were all constrained to the cis isomers. Although no proof of the geometry of the enediol in 55 was available, it is possible that the enediol in this system is trans. This arrangement would lead to a reduced dipole moment and thus an inherently more stable system.
45. Castro, C. E.; Gaugahn, E. G.; Owsley, D. C. J. Org. Chem. 1966, 31, 4071-4078.
46. Miyazawa, T.; Endo, T.; Shiihashi, S.; Okawara, M. J. Org. Chem. 1985 50, 1332-1334.