Progress toward the total synthesis of (+)-aldosterone: Synthesis of the A-D rings

Organic Letters

Volumn 5, Issue 10, 2003, Pages 1613-1616

  Bear, Brian R ^a   Parnes, Jason S ^a   Shea, Kenneth J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOSTERONE; STEROID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; DIELS ALDER REACTION; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HORMONE SYNTHESIS; REACTION ANALYSIS; RING OPENING; STRUCTURE ANALYSIS; X RAY ANALYSIS; CHEMICAL STRUCTURE; CONFORMATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALDOSTERONE; CRYSTALLOGRAPHY, X-RAY; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 0042229242     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034218c     Document Type: Article

References (40)

1. (a) Voet, D.; Voet, J. Biochemistry, 2nd ed.; John Wiley & Sons: New York, 1995; p 1269.
2. (b) Campbell, N. A.; Reece, J. B.; Mitchell, L. G. Biology, 5th ed.; Benjamin/Cummings: Menlo Park, CA, 1999; pp 908-909.
3. Simpson, S. A.; Tait, J. F.; Wettstein, A.; Neher, R.; von Euw, J.; Reichstein, T. Experientia 1953, 9, 333-335.
4. Schmidlin, J.; Anner, G.; Billeter, J. R.; Wettstein, A. Experientia 1955, 11, 365-368.
5. Johnson, W. S.; et al. J. Am. Chem. Soc. 1963, 85, 1409-1430.
6. (a) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1960, 82, 2640-2641.
7. (b) Barton, D. H. R.; Beaton, J. M. J. Am. Chem. Soc. 1960, 82, 2640.
8. (c) Barton, D. H. R.; Beaton, J. M. J. Am. Chem. Soc. 1961, 83, 4083-4089.
9. (d) Barton, D. H. R.; et al. J. Chem. Soc., Perkin Trans. 1 1975, 2243-2251.
10. For additional studies of the synthesis of aldosterone, see: (a) von Euw, J.; Neher, R.; Reichstein, T. Helv. Chim. Acta 1955, 38, 1423-1437. (b) Lardon, A.; Schindler, O.; Reichstein, T. Helv. Chim. Acta 1957, 40, 666-704. (c) van der Burg, W. J.; et al. Recl. Trav. Chim. Pays-Bas 1958, 77, 171-176. (d) Szpilfogel, S. A.; van der Burg, W. J.; Siegmann, C. M.; van Dorp, D. A. Recl. Trav. Chim. Pays-Bas 1956, 75, 1043-1052. (e) Schmidlin, J.; et al. Helv. Chim. Acta 1957, 40, 1034-1051. (f) Vischer, E.; Schmidlin, J.; Wettstein, A. Experientia 1956, 12, 50-52. (g) Schmidlin, J.; Wettstein, A. Helv. Chim. Acta 1962, 45, 331-347. (h) Miyano, M. J. Org. Chem. 1981, 46, 1845-1853.
11. For additional studies of the synthesis of aldosterone, see: (a) von Euw, J.; Neher, R.; Reichstein, T. Helv. Chim. Acta 1955, 38, 1423-1437. (b) Lardon, A.; Schindler, O.; Reichstein, T. Helv. Chim. Acta 1957, 40, 666-704. (c) van der Burg, W. J.; et al. Recl. Trav. Chim. Pays-Bas 1958, 77, 171-176. (d) Szpilfogel, S. A.; van der Burg, W. J.; Siegmann, C. M.; van Dorp, D. A. Recl. Trav. Chim. Pays-Bas 1956, 75, 1043-1052. (e) Schmidlin, J.; et al. Helv. Chim. Acta 1957, 40, 1034-1051. (f) Vischer, E.; Schmidlin, J.; Wettstein, A. Experientia 1956, 12, 50-52. (g) Schmidlin, J.; Wettstein, A. Helv. Chim. Acta 1962, 45, 331-347. (h) Miyano, M. J. Org. Chem. 1981, 46, 1845-1853.
12. For additional studies of the synthesis of aldosterone, see: (a) von Euw, J.; Neher, R.; Reichstein, T. Helv. Chim. Acta 1955, 38, 1423-1437. (b) Lardon, A.; Schindler, O.; Reichstein, T. Helv. Chim. Acta 1957, 40, 666-704. (c) van der Burg, W. J.; et al. Recl. Trav. Chim. Pays-Bas 1958, 77, 171-176. (d) Szpilfogel, S. A.; van der Burg, W. J.; Siegmann, C. M.; van Dorp, D. A. Recl. Trav. Chim. Pays-Bas 1956, 75, 1043-1052. (e) Schmidlin, J.; et al. Helv. Chim. Acta 1957, 40, 1034-1051. (f) Vischer, E.; Schmidlin, J.; Wettstein, A. Experientia 1956, 12, 50-52. (g) Schmidlin, J.; Wettstein, A. Helv. Chim. Acta 1962, 45, 331-347. (h) Miyano, M. J. Org. Chem. 1981, 46, 1845-1853.
13. For additional studies of the synthesis of aldosterone, see: (a) von Euw, J.; Neher, R.; Reichstein, T. Helv. Chim. Acta 1955, 38, 1423-1437. (b) Lardon, A.; Schindler, O.; Reichstein, T. Helv. Chim. Acta 1957, 40, 666-704. (c) van der Burg, W. J.; et al. Recl. Trav. Chim. Pays-Bas 1958, 77, 171-176. (d) Szpilfogel, S. A.; van der Burg, W. J.; Siegmann, C. M.; van Dorp, D. A. Recl. Trav. Chim. Pays-Bas 1956, 75, 1043-1052. (e) Schmidlin, J.; et al. Helv. Chim. Acta 1957, 40, 1034-1051. (f) Vischer, E.; Schmidlin, J.; Wettstein, A. Experientia 1956, 12, 50-52. (g) Schmidlin, J.; Wettstein, A. Helv. Chim. Acta 1962, 45, 331-347. (h) Miyano, M. J. Org. Chem. 1981, 46, 1845-1853.
14. For additional studies of the synthesis of aldosterone, see: (a) von Euw, J.; Neher, R.; Reichstein, T. Helv. Chim. Acta 1955, 38, 1423-1437. (b) Lardon, A.; Schindler, O.; Reichstein, T. Helv. Chim. Acta 1957, 40, 666-704. (c) van der Burg, W. J.; et al. Recl. Trav. Chim. Pays-Bas 1958, 77, 171-176. (d) Szpilfogel, S. A.; van der Burg, W. J.; Siegmann, C. M.; van Dorp, D. A. Recl. Trav. Chim. Pays-Bas 1956, 75, 1043-1052. (e) Schmidlin, J.; et al. Helv. Chim. Acta 1957, 40, 1034-1051. (f) Vischer, E.; Schmidlin, J.; Wettstein, A. Experientia 1956, 12, 50-52. (g) Schmidlin, J.; Wettstein, A. Helv. Chim. Acta 1962, 45, 331-347. (h) Miyano, M. J. Org. Chem. 1981, 46, 1845-1853.
15. For additional studies of the synthesis of aldosterone, see: (a) von Euw, J.; Neher, R.; Reichstein, T. Helv. Chim. Acta 1955, 38, 1423-1437. (b) Lardon, A.; Schindler, O.; Reichstein, T. Helv. Chim. Acta 1957, 40, 666-704. (c) van der Burg, W. J.; et al. Recl. Trav. Chim. Pays-Bas 1958, 77, 171-176. (d) Szpilfogel, S. A.; van der Burg, W. J.; Siegmann, C. M.; van Dorp, D. A. Recl. Trav. Chim. Pays-Bas 1956, 75, 1043-1052. (e) Schmidlin, J.; et al. Helv. Chim. Acta 1957, 40, 1034-1051. (f) Vischer, E.; Schmidlin, J.; Wettstein, A. Experientia 1956, 12, 50-52. (g) Schmidlin, J.; Wettstein, A. Helv. Chim. Acta 1962, 45, 331-347. (h) Miyano, M. J. Org. Chem. 1981, 46, 1845-1853.
16. For additional studies of the synthesis of aldosterone, see: (a) von Euw, J.; Neher, R.; Reichstein, T. Helv. Chim. Acta 1955, 38, 1423-1437. (b) Lardon, A.; Schindler, O.; Reichstein, T. Helv. Chim. Acta 1957, 40, 666-704. (c) van der Burg, W. J.; et al. Recl. Trav. Chim. Pays-Bas 1958, 77, 171-176. (d) Szpilfogel, S. A.; van der Burg, W. J.; Siegmann, C. M.; van Dorp, D. A. Recl. Trav. Chim. Pays-Bas 1956, 75, 1043-1052. (e) Schmidlin, J.; et al. Helv. Chim. Acta 1957, 40, 1034-1051. (f) Vischer, E.; Schmidlin, J.; Wettstein, A. Experientia 1956, 12, 50-52. (g) Schmidlin, J.; Wettstein, A. Helv. Chim. Acta 1962, 45, 331-347. (h) Miyano, M. J. Org. Chem. 1981, 46, 1845-1853.
17. For additional studies of the synthesis of aldosterone, see: (a) von Euw, J.; Neher, R.; Reichstein, T. Helv. Chim. Acta 1955, 38, 1423-1437. (b) Lardon, A.; Schindler, O.; Reichstein, T. Helv. Chim. Acta 1957, 40, 666-704. (c) van der Burg, W. J.; et al. Recl. Trav. Chim. Pays-Bas 1958, 77, 171-176. (d) Szpilfogel, S. A.; van der Burg, W. J.; Siegmann, C. M.; van Dorp, D. A. Recl. Trav. Chim. Pays-Bas 1956, 75, 1043-1052. (e) Schmidlin, J.; et al. Helv. Chim. Acta 1957, 40, 1034-1051. (f) Vischer, E.; Schmidlin, J.; Wettstein, A. Experientia 1956, 12, 50-52. (g) Schmidlin, J.; Wettstein, A. Helv. Chim. Acta 1962, 45, 331-347. (h) Miyano, M. J. Org. Chem. 1981, 46, 1845-1853.
18. Bear, B. R.; Sparks, S. M.; Shea, K. J. Angew. Chem., Int. Ed. 2001, 40, 821-849.
19. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277.
20. (a) Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J., Tetrahedron 1998, 54, 2289-2338.
21. (b) Shea, K. J.; Zandi, K. S.; Staab, A. J.; Carr, R. Tetrahedron Lett. 1990, 31, 5885-5888.
22. (c) Shea, K. J.; Staab, A. J.; Zandi, K. S. Tetrahedron Lett. 1991, 32, 2715-2718.
23. Shea, K. J.; Gauthier, D. R., Jr. Tetrahedron Lett. 1994, 35, 7311-7314.
24. Dzierba, C. D.; Zandi, K. S.; Mollers, T.; Shea, K. J. J. Am. Chem. Soc. 1996, 118, 4711-4712.
25. Compound 6 was prepared by coupling methyl acrylate and trans-cinnamaldehyde under Baylis-Hillman conditions followed by acetylation of the resulting alcohol and an acetate transposition procedure developed by Foucaud and E1 Guemmout. See Supporting Information and ref 13.
26. Foucaud, A.; El Guemmout, F. Bull. Soc. Chim. Fr. 1989, 3, 403-408.
27. Meth-Cohn, O. J. Chem. Soc., Chem. Commun. 1986, 695-607.
28. Crosby, J.; Stoddart, J. F.; Sun, X.; Venner, M. R. W. Synthesis 1993, 141-145.
29. Stotter, P. L.; Eppner, J. B. Tetrahedron Lett. 1973, 26, 2417-2420.
30. Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624-2626.
31. (a) Swaminathan, S.; Newman, M. S. Tetrahedron 1958, 2, 88-99.
32. (b) Ramakrishnan, V. T.; Ramachandra, S.; Venkataramani, P. S.; Swaminathan, S. Tetrahedron 1967, 23, 2453-2459.
33. (c) Darvesh, S.; Grant, A. S.; MaGee, D. I.; Valenta, Z. Can J. Chem. 1989, 67, 2237-2240.
34. (d) Swaminathan, S.; Narayanan, K. V. Chem. Rev. 1971, 71, 429-438.
35. (a) Bernstein, S.; Lenhard, R. H.; Williams, J. H. J. Org. Chem. 1953, 18, 1166-1176.
36. (b) Zderic, J. A.; Iriarte, J. J. Org. Chem. 1962, 27, 1756-1760.
37. (c) Oliveto, E. P.; Clayton, T.; Hershberg, E. B. J. Am. Chem. Soc. 1953, 75, 486-488.
38. (d) Oliveto, E. P.; et al. J. Am. Chem. Soc. 1956, 78, 1736-1738.
39. Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G. Tetrahedron Lett. 1987, 28, 5287-5290.
40. Lin, R.; Castells, J.; Rapoport, H. J. Org. Chem. 1998, 63, 4069-4078.