An ascending synthesis of adrenalcorticosteroids. The total synthesis of (+)-adrenosterone

Journal of the American Chemical Society

Volumn 118, Issue 19, 1996, Pages 4711-4712

  Dzierba, Carolyn D ^a   Zandi, Kathleen S ^a   Möllers, Thomas ^a   Shea, K J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADRENOSTERONE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0029992817     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9602509     Document Type: Article

References (45)

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7. For previous syntheses, see: (a) Velluz, L.; Nominé, G.; Mathieu, J.; Toromanoff, E.; Bertin, D.; Bucourt, R.; Tessier, J. Compt. Rendu 1960, 250, 1293. (b) Stork, G.; Winkler, J. D.; Shiner, C. S. J. Am. Chem. Soc. 1982, 104, 3767. (c) Stork, G.; Saccomano, N. A. Tetrahedron Lett. 1987, 28, 2087. (d) Van Royen, L. A.; Mijngheer, R.; De Clercq, P. J. Tetrahedron 1985, 41, 4667. (e) Kametani, T.; Matsumoto, H.; Honda, T.; Nagai, M.; Fukumoto, K. Tetrahedron 1981, 37, 2555. (f) Horiguchi, Y.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1989, 111, 6257.
8. For previous syntheses, see: (a) Velluz, L.; Nominé, G.; Mathieu, J.; Toromanoff, E.; Bertin, D.; Bucourt, R.; Tessier, J. Compt. Rendu 1960, 250, 1293. (b) Stork, G.; Winkler, J. D.; Shiner, C. S. J. Am. Chem. Soc. 1982, 104, 3767. (c) Stork, G.; Saccomano, N. A. Tetrahedron Lett. 1987, 28, 2087. (d) Van Royen, L. A.; Mijngheer, R.; De Clercq, P. J. Tetrahedron 1985, 41, 4667. (e) Kametani, T.; Matsumoto, H.; Honda, T.; Nagai, M.; Fukumoto, K. Tetrahedron 1981, 37, 2555. (f) Horiguchi, Y.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1989, 111, 6257.
9. For previous syntheses, see: (a) Velluz, L.; Nominé, G.; Mathieu, J.; Toromanoff, E.; Bertin, D.; Bucourt, R.; Tessier, J. Compt. Rendu 1960, 250, 1293. (b) Stork, G.; Winkler, J. D.; Shiner, C. S. J. Am. Chem. Soc. 1982, 104, 3767. (c) Stork, G.; Saccomano, N. A. Tetrahedron Lett. 1987, 28, 2087. (d) Van Royen, L. A.; Mijngheer, R.; De Clercq, P. J. Tetrahedron 1985, 41, 4667. (e) Kametani, T.; Matsumoto, H.; Honda, T.; Nagai, M.; Fukumoto, K. Tetrahedron 1981, 37, 2555. (f) Horiguchi, Y.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1989, 111, 6257.
10. For previous syntheses, see: (a) Velluz, L.; Nominé, G.; Mathieu, J.; Toromanoff, E.; Bertin, D.; Bucourt, R.; Tessier, J. Compt. Rendu 1960, 250, 1293. (b) Stork, G.; Winkler, J. D.; Shiner, C. S. J. Am. Chem. Soc. 1982, 104, 3767. (c) Stork, G.; Saccomano, N. A. Tetrahedron Lett. 1987, 28, 2087. (d) Van Royen, L. A.; Mijngheer, R.; De Clercq, P. J. Tetrahedron 1985, 41, 4667. (e) Kametani, T.; Matsumoto, H.; Honda, T.; Nagai, M.; Fukumoto, K. Tetrahedron 1981, 37, 2555. (f) Horiguchi, Y.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1989, 111, 6257.
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14. For examples of the type 2 intramolecular Diels-Alder reaction, see: (a) Shea, K. J.; Wise, S J. Am. Chem. Soc. 1978, 100, 6519. (b) Shea, K. J.; Beauchamp, P. S.; Lind, R. J. Am. Chem. Soc. 1980, 102, 4544. (c) Shea, K. J.; Wise, S.; Burke, L. D.; Davis, P. D.; Gilman, J. W., Greeley, A. C. J. Am. Chem. Soc. 1982, 104, 5708. (d) Shea, K. J.; Wada, E. J. Am. Chem. Soc. 1982, 104, 5715. (e) Shea, K. J., Davis, P. D. Angew. Chem., Int. Ed. Engl. 1983, 22, 419; Angew. Chem. Suppl. 1983, 564-570. (f) Shea, K. J.; Burke, L. D.; England, W. P. J. Am. Chem. Soc. 1988, 110, 860. (g) Shea, K. J.; Lease, T. G.; Ziller, J. W. J. Am. Chem. Soc. 1990, 112, 8627. (h) Lease, T. G.; Shea, K. J. J. Am. Chem. Soc., 1993, 115, 2248
15. For examples of the type 2 intramolecular Diels-Alder reaction, see: (a) Shea, K. J.; Wise, S J. Am. Chem. Soc. 1978, 100, 6519. (b) Shea, K. J.; Beauchamp, P. S.; Lind, R. J. Am. Chem. Soc. 1980, 102, 4544. (c) Shea, K. J.; Wise, S.; Burke, L. D.; Davis, P. D.; Gilman, J. W., Greeley, A. C. J. Am. Chem. Soc. 1982, 104, 5708. (d) Shea, K. J.; Wada, E. J. Am. Chem. Soc. 1982, 104, 5715. (e) Shea, K. J., Davis, P. D. Angew. Chem., Int. Ed. Engl. 1983, 22, 419; Angew. Chem. Suppl. 1983, 564-570. (f) Shea, K. J.; Burke, L. D.; England, W. P. J. Am. Chem. Soc. 1988, 110, 860. (g) Shea, K. J.; Lease, T. G.; Ziller, J. W. J. Am. Chem. Soc. 1990, 112, 8627. (h) Lease, T. G.; Shea, K. J. J. Am. Chem. Soc., 1993, 115, 2248
16. For examples of the type 2 intramolecular Diels-Alder reaction, see: (a) Shea, K. J.; Wise, S J. Am. Chem. Soc. 1978, 100, 6519. (b) Shea, K. J.; Beauchamp, P. S.; Lind, R. J. Am. Chem. Soc. 1980, 102, 4544. (c) Shea, K. J.; Wise, S.; Burke, L. D.; Davis, P. D.; Gilman, J. W., Greeley, A. C. J. Am. Chem. Soc. 1982, 104, 5708. (d) Shea, K. J.; Wada, E. J. Am. Chem. Soc. 1982, 104, 5715. (e) Shea, K. J., Davis, P. D. Angew. Chem., Int. Ed. Engl. 1983, 22, 419; Angew. Chem. Suppl. 1983, 564-570. (f) Shea, K. J.; Burke, L. D.; England, W. P. J. Am. Chem. Soc. 1988, 110, 860. (g) Shea, K. J.; Lease, T. G.; Ziller, J. W. J. Am. Chem. Soc. 1990, 112, 8627. (h) Lease, T. G.; Shea, K. J. J. Am. Chem. Soc., 1993, 115, 2248
17. For examples of the type 2 intramolecular Diels-Alder reaction, see: (a) Shea, K. J.; Wise, S J. Am. Chem. Soc. 1978, 100, 6519. (b) Shea, K. J.; Beauchamp, P. S.; Lind, R. J. Am. Chem. Soc. 1980, 102, 4544. (c) Shea, K. J.; Wise, S.; Burke, L. D.; Davis, P. D.; Gilman, J. W., Greeley, A. C. J. Am. Chem. Soc. 1982, 104, 5708. (d) Shea, K. J.; Wada, E. J. Am. Chem. Soc. 1982, 104, 5715. (e) Shea, K. J., Davis, P. D. Angew. Chem., Int. Ed. Engl. 1983, 22, 419; Angew. Chem. Suppl. 1983, 564-570. (f) Shea, K. J.; Burke, L. D.; England, W. P. J. Am. Chem. Soc. 1988, 110, 860. (g) Shea, K. J.; Lease, T. G.; Ziller, J. W. J. Am. Chem. Soc. 1990, 112, 8627. (h) Lease, T. G.; Shea, K. J. J. Am. Chem. Soc., 1993, 115, 2248
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