Facile C21 functionalization through a novel functional group transfer reaction in 16α,17α-epoxy-3β-hydroxypregn-5-en-20-one and its applications

Chemical Communications

Volumn 2, Issue 18, 2002, Pages 2102-2103

  Girdhar, Navdeep K ^a   Ishar, Mohan Paul S ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

16ALPHA,17ALPHA EPOXY 3BETA HYDROXYPREGN 5 EN 20 ONE; 21 CHLORO 3BETA HYDROXYPREGN 5,16 DIEN 20 ONE; FUNCTIONAL GROUP; HYDROCHLORIC ACID; STEROID; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0036399585     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b205022f     Document Type: Article

References (20)

1. D. N. Kirk and M. P. Hartshorn, in Steroid Reaction Mechanisms Elsevier, Amsterdam, 1968, p. 394
2. C. W. Shoppee, in Chemistry of the Steroids Butterworths, London, 1964, ch. 4, p. 245
3. J. Fried and J. A. Edwards, in Organic Reactions in Steroid Chemistry Van Nostrand Reinhold Company, New York, 1972, vol. 1 & 2
4. J. M. McCall, E. J. Jacobsen, F. J. Van-Doornik, J. R. Palmer, H. J. Karnes, Patent,?Pub Caret? PCT Int. WO 87 01, 706: Chem. Abstr., 1988, 108, 6287u.
5. E. J. Jacobsen, J. M. McCall, D. E. Ayer, F. J. Van-Doornik, J. R. Palmer, K. L. Belonga, J. M. Braughler, D. E. Hall, D. J. Houser, J. Med. Chem., 1990, 33, 1145.
6. N. H. Baine, F. F. Owings, D. N. Kline, T. Resnick, L.-J. Ping, M. Fox, R. E. Mewshaw, A. M. Tickner, C. J. Kawalski, J. Conard, J. Org. Chem., 1994, 59, 5987.
7. J. E. Cabaj, P. G. M. Wuts, K. E. Henegar, J. Org. Chem., 1994, 59, 5090.
8. R. A. Cadenas, J. Mosetting, M. E. Gelpi, Steroids, 1996, 61, 703.
9. A. X. Yan, G. W. Xing, Y. H. Ye, G. L. Tian, M. S. Wong, K. S. Lee, Tetrahedron Lett., 2000, 41, 5379.
10. P. L. Julian, E. W. Meyer, W. J. Karpel, I. R. Waller, J. Am. Chem. Soc., 1950, 72, 5145.
11. A. J. Warings, in Comprehensive Organic Chemistry ed. D. R. H. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979, 1, p. 1036
12. P. Brownbridge, Synthesis, 1983, 85.
13. L. Blanco, P. Amice, J. M. Conia, Synthesis, 1976, 194.
14. R. H. Reuss, A. Hassner, J. Org. Chem., 1974, 39, 1785.
15. M. J. S. M. Moreno, M. L. Sa e Melo, A. S. C. Neves, Synlett, 1994, 651.
16. J.-H. Sheu, S.-P. Chen, P.-J. Sung, M. Y. Chang, C.-F. Dai, Tetrahedron Lett., 2000, 41, 7885.
17. H. J. Reich, M. Jautelat, M. T. Messe, F. J. Weigert, J. D. Roberts, J. Am. Chem. Soc., 1969, 91, 7445.
18. 13C NMR Spectroscopy of Steroids’, Annual Report on NMR Spectroscopy 1978, vol. 8, p. 199
19. E. Breitmair and W. Voelter, in Carbon-13 NMR spectroscopy VCH, New York, 1987
20. B. M. Bain, G. H. Phillipps, P. A. Procopiou, I. P. Steeples, R. J. Upton, J. Org. Chem., 1998, 63, 7421.