A new strategy for the preparation of 11-oxygenated steroids synthesis of (±)-adrenosterone

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7047-7050

  Grieco, Paul A ^a   May, Scott A ^a   Kaufman, Michael D ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

11 HYDROXYCORTICOSTEROID; ADRENOSTERONE; STEROID;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CONJUGATION; STEROIDOGENESIS;

OXY;

EID: 0032563816     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01526-3     Document Type: Article

References (18)

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4. (d) Nemoto, H.; Nagai, M.; Moizumi, M.; Kohzuki, K.; Fukumoto, K.; Kametani, T. Tetrahedron Lett. 1988, 29, 4959.
5. 2. MMX calculations indicate that 3 is 6.6 kcal lower in energy than cycloadduct 7.
6. 2O afforded (86%) tricyclic ketone iv with no trace of the anticipated cycloadduct being detected. Also, in the case of iii → iv, this transformation could be brought about in 81% yield employing 0.1 equiv of boron trifluoride etherate in methylene chloride at 0 °C (1h). (Formula Presented)
7. 4. Grieco, P. A.; Cooke, R. J.; Henry, K. J.; VanderRoest, J. M. Tetrahedron Lett. 1991, 32, 4665.
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12. 9. For the use of unsaturated oxycarbenium ions in Diels-Alder reactions, see: Roush, W. R.; Gillis, H. R.; Essenfeld, A. P. J. Org. Chem. 1984, 49, 4674. Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182. Grieco, P. A.; Collins, J. L.; Handy, S. T. Syn. Lett. 1995, 1155. Baldwin, J. E.; Chesworth, R.; Parker, J. S.; Russell, A. T. Tetrahedron Lett. 1995, 36, 9551.
13. 9. For the use of unsaturated oxycarbenium ions in Diels-Alder reactions, see: Roush, W. R.; Gillis, H. R.; Essenfeld, A. P. J. Org. Chem. 1984, 49, 4674. Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182. Grieco, P. A.; Collins, J. L.; Handy, S. T. Syn. Lett. 1995, 1155. Baldwin, J. E.; Chesworth, R.; Parker, J. S.; Russell, A. T. Tetrahedron Lett. 1995, 36, 9551.
14. 9. For the use of unsaturated oxycarbenium ions in Diels-Alder reactions, see: Roush, W. R.; Gillis, H. R.; Essenfeld, A. P. J. Org. Chem. 1984, 49, 4674. Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182. Grieco, P. A.; Collins, J. L.; Handy, S. T. Syn. Lett. 1995, 1155. Baldwin, J. E.; Chesworth, R.; Parker, J. S.; Russell, A. T. Tetrahedron Lett. 1995, 36, 9551.
15. 9. For the use of unsaturated oxycarbenium ions in Diels-Alder reactions, see: Roush, W. R.; Gillis, H. R.; Essenfeld, A. P. J. Org. Chem. 1984, 49, 4674. Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182. Grieco, P. A.; Collins, J. L.; Handy, S. T. Syn. Lett. 1995, 1155. Baldwin, J. E.; Chesworth, R.; Parker, J. S.; Russell, A. T. Tetrahedron Lett. 1995, 36, 9551.
16. 10. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357.
17. -3 (Z = 4). For more information, contact Dr. John C. Huffman, Indiana University, Department of Chemistry, Molecular Structure Center, Bloomington, Indiana 47405, Report # 96118. (Formula Presented)
18. 12. Wenkert, E.; Ferreira, T. W.; Michelotti, E. L. J. Chem. Soc., Chem. Commun. 1979, 637.