Studies directed towards the total synthesis of aldosterone and naturally occurring analogues. A unified approach using the transannular Diels-Alder reaction

Tetrahedron

Volumn 54, Issue 8, 1998, Pages 1529-1562

  Couturier, Michel ^a   Dory, Yves L ^a   Rouillard, François ^a   Deslongchamps, Pierre ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOSTERONE; ALDOSTERONE DERIVATIVE; ALPHA CHLOROKETONE; BETA OXOCARBOXYLIC ACID ESTER; MACROCYCLIC COMPOUND; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; CYCLIZATION; HORMONE SYNTHESIS; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL;

EID: 0032546091     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10393-3     Document Type: Article

References (57)

1. 1. Simpson, S. A.; Tait, J. F. Endocrinology 1952, 50, 150.
2. (b) Simpson, S. A.; Tait, J. F.; Wettstein, A.; Neher, R.; von Euw Schindler, J.; Reichstein, T. Helv. Chim. Acta 1954, 37, 1163.
3. 2. Gómez Sánchez, E. P. Steroids 1995, 60, 69.
4. 3. Young, M. J.; Funder, J. W. Steroids 1995, 60, 233.
5. 4. (a) Velluz, L.; Muller, G.; Bardoneschi, R.; Poittevin, A. Compt. rend. 1960, 250, 725.
6. (b) Wolff, M. E.; Kerwin, J. F.; Owings, F. F.; Lewis, B. B.; Blank, B.; Magnani, A.; Georgian, V. J. Am. Chem. Soc. 1960, 82, 4117.
7. (c) Heusler, K.; Kalvoda, J.; Meystre, C.; Wieland, P.; Anner, G.; Wettstein, A.; Cainelli, G.; Arigoni, D.; Jeger, O. Helv. Chim. Acta 1961, 34, 502, 1374.
8. (d) Barton, D. H. R.; Beaton, J. M. J. Am. Chem. Soc. 1961, 83, 4083.
9. (e) Barton, D. H. R.; Basu, N. K.; Day, M. J.; Hesse, R. H.; Pechet, M. M.; Starratt, A. N. J. Chem. Soc. Perkin I 1975, 2243.
10. (f) Miyano, M. J. Org. Chem. 1981, 46, 1846.
11. 5. (a) Vischer, E.; Schmidlin, J.; Wettstein, A. Experientia 1956, 12, 50.
12. (b) Schmidlin, J.; Anner, G.; Billeter, J. R.; Heusler, K.; Ueberwasser, H.; Wieland, P.; Wettstein, A. Helv. Chim. Acta 1957, 40, 1034, 1438, 2291.
13. (c) Lardon, A.; Schindler, O.; Reichstein, T. Helv. Chim. Acta 1957, 40, 666.
14. (d) van der Burg, W. J.; van Dorp, D. A.; Schindler, O.; Siegmann, C. M.; Szpilfogel, S. A. Recl. Trav. Chim. Pays Bas 1958, 77, 171.
15. (e) (f) Heusler, K.; Wieland, P.; Wettstein, A. Helv. Chim. Acta 1959, 42, 1586.
16. (g) Johnson, W. S.; Collins, J. C.; Pappo, R.; Rubin, M. B.; Kropp, P. J.; Johns, W. F.; Pike, J. E.; Bartmann, W. J. Am. Chem. Soc. 1963, 85, 1409.
17. 6. (a) Harnik, M.; Kashman, Y.; Aharonowitz, Y.; Morris, D. J. J. Steroid Biochem. 1985, 23, 207.
18. (b) Harnik, M.; Kashman, Y.; Cojocaru, M.; Rosenthal, T.; Morris, D. J. J. Steroid Biochem. 1986, 24, 1163.
19. 7. Harnik, M.; Kashman, Y.; Carmely, S.; Cojocaru, M.; Dale, S. L.; Holbrook, M. M.; Melby, J. C. Steroids 1986, 47, 67.
20. 8. Deslongchamps, P. Pure Appl. Chem. 1992, 64, 1831.
21. 9. (a) Couturier, M.; Deslongchamps P. Synlett 1996, 1140.
22. (b) Marinier, A.; Deslongchamps, P. Can. J. Chem. 1992, 70, 2350.
23. (c) Marinier, A.; Deslongchamps, P. Tetrahedron Lett. 1988, 29, 6215.
24. 10. (a) Urban, E.; Knühl, G.; Helmchen, G. Tetrahedron 1996, 52, 971.
25. (b) Urban, E.; Knühl, G.; Helmchen, G. Tetrahedron Lett. 1995, 36, 7229.
26. 11. Nugent, W. A.; Hobbs, F. W., Jr. Org. Synth. 1988, 66, 52.
27. 12. Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 2173.
28. 13. Schlosser, M.; Zhang, X.-p. Tetrahedron Lett. 1993, 34, 1925.
29. 14. Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813.
30. 15. Jung, M. E.; Light, L. A. Tetrahedron Lett. 1982, 23, 3851.
31. 16. Collington, E. W.; Meyers, A. I. J. Org. Chem. 1971, 36, 3044.
32. 17. (a) Schmid, C. R.; Bryant, J. D. Org. Synth. 1995, 72,
33. (b) Schmid, C. R.; Bryant, J. D.; Dowlatzedah, M.; Phillips, J. L.; Prather, D. E.; Schantz, R. D.; Sear, N. L.; Vianco, C. S. J. Org. Chem. 1991, 56, 4056.
34. 18. Trippett, S. Advan. Org. Chem. 1960, 1, 83.
35. 19. Salmond, W. G.; Barta, M. A.; Havens, J. L. J. Org. Chem. 1978, 43, 790.
36. 20. Flizar, S.; Hudson, R. F.; Salvadori, G.; Helv. Chim. Acta 1963, 46, 1580.
37. 21. Howe, A. A.; Manni, P. E.; Cassady, J. M. J. Med. Chem. 1974, 17, 840.
38. 22. (a) Tufariello, J. J.; Kissel, W. J. Tetrahedron Lett. 1966, 49, 6145.
39. (b) Corey, E. J.; Wollenberg, R. H.; Williams, D. R. Tetrahedron Lett. 1977, 60, 2243.
40. (c) Wasserman, H. H.; Lipshutz, B. H. Tetrahedron Lett. 1975, 51, 4611.
41. (d) Toussaint, O.; Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1984, 25, 3819
42. 23. Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
43. 24. Suzuki, T.; Sato, E.; Unno, K.; Kametani, T. J. Chem. Soc., Perkin Trans. I 1986, 2263.
44. 25. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
45. 26. Magid, R. M.; Fruchey, O. S.; Johnson, W. L.; Allen, T. G. J. Org. Chem. 1979, 44, 359.
46. 27. (a) Jung, S. H.; Lee, Y. S.; Park, H.; Kwon, D.-S. Tetrahedron Lett. 1995, 36, 1051.
47. (b) Roush, W. R.; Warmus, J. S.; Works, A. B. Tetrahedron Lett. 1993, 34, 4427.
48. (c) Takahashi, T; Sakamoto, Y.; Doi, T. Tetrahedron Lett. 1992, 33, 3519.
49. 28. Dory, Y. L.; Soucy, P.; Drouin, M.; Deslongchamps, P. J. Am. Chem. Soc. 1995, 117, 518.
50. 29. Drouin, M.; Couturier, M.; Deslongchamps, P. Acta Cryst. Submitted.
51. 30. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
52. 31. Stewart, J. J. P. QCPE No 455.
53. 32. Semiempirical computational procedure: All the calculations were done at the RHF level. The first input files for MOPAC 6.00 were created by means of SYBYL 6.01 (Tripos Associates, Inc.: 16995 Hanley Rd, Suite 303, St. Louis, MO 63144-2913) for IBM RS/6000 computers. The norm of the gradient of these draft structures were then fully optimized using TS subroutines. Finally, all the transition structures were characterized by only one negative force constant.
54. 33. Dory, Y. L.; Ouellet, C.; Berthiaume, S.; Favre, A.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1994, 131, 121.
55. 34. Barriault, L.; Ouellet, S.G.; Deslongchamps, P. Tetrahedron. In press.
56. 35. (a) Chan, T. H.; Brook, M. A.; Chaly, T. Synthesis, 203.
57. (b) Loewenthal, H. J. E. Tetrahedron 1959, 6, 269.