Mechanistic studies of deoxygenation of steroidal ring-D 16,17-ketols with trimethylsilyl iodide

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 4, 1999, Pages 548-553

  Nagaoka, Masao ^a   Nagasawa, Etsuko ^a   Sato, Sadao ^b   Numazawa, Mitsuteru ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

^b DAIICHI SANKYO CO   (Japan)

Author keywords

16 hydroxy 17 keto steroid; 17 hydroxy 16 keto steroid; Deoxygenation; Steroid dimer; Trimethylsilyl iodide

Indexed keywords

16 HYDROXY 17 KETO STEROID; 17BETA HYDROXY 16 KETO STEROID; KETOL; ORGANOSILICON DERIVATIVE; TRIMETHYLSILYL IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; IODINATION; ORGANIC CHEMISTRY; OXYGENATION; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS;

EID: 0032924210     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.548     Document Type: Article

References (22)

1. Olah G. A., Narang S. C., Tetrahedron, 38, 2225-2277 (1982).
2. Ho T. L., Synth. Commun., 9, 665-668 (1979).
3. Sarma D. N., Sarma J. C., Barua N. C., Sharma R. P., J. Chem. Soc., Chem. Commun., 1984, 813-814.
4. Sarma J. C., Barua N. C., Sharma R. P., Barua J. N., Tetrahedron, 39, 2843-2846 (1983).
5. Denis J. N., Magane R., Eenoo M. V., Krief A., Neuv. J. Chim., 3, 705-707 (1979); Jung K.-Y., Koreeda M., J. Org. Chem., 54, 5667-5675 (1989).
6. Denis J. N., Magane R., Eenoo M. V., Krief A., Neuv. J. Chim., 3, 705-707 (1979); Jung K.-Y., Koreeda M., J. Org. Chem., 54, 5667-5675 (1989).
7. Hartman D. A., Curley Jr. R. W., Tetrahedron Lett., 30, 645-646 (1989).
8. a) Numazawa M. , Nagaoka M., Kunitama Y., J. Chem. Soc., Chem. Commun., 1984, 31-32;
9. b) Numazawa M., Nagaoka M., Kunitama Y., Chem. Pharm. Bull., 34, 3722-3726 (1986).
10. Nagaoka M., Kunitama Y., Numazawa M., J. Org. Chem., 56, 334-338 (1991).
11. Nagaoka M., Nagasawa E., Numazawa M., Chem. Pharm. Bull., 46, 1857-1861 (1998).
12. Leeds N. S., Fukushima D. K., Gallagher T. F., J. Am. Chem. Soc., 76, 2943-2948 (1954); Fishman J., J. Am. Chem. Soc., 82, 6143-6147 (1960).
13. Leeds N. S., Fukushima D. K., Gallagher T. F., J. Am. Chem. Soc., 76, 2943-2948 (1954); Fishman J., J. Am. Chem. Soc., 82, 6143-6147 (1960).
14. Olah G. A., Arvanaghi M., Vankar Y. D., J. Org. Chem., 45, 3531-3532 (1980).
15. Doyle M. P., DeBruyn D. J., Kooistra D. A., J. Am. Chem. Soc., 94, 3659-3661 (1972).
16. Sassaman M. B., Kotian K. D., Surya Prakash G. K., Olah G. A., J. Org. Chem., 52, 4314-4319 (1987).
17. Combe M. G., Denny W. A., Meakins G. D., Morisawa Y., Richards E. E., J. Chem. Soc., (C), 1971, 2300-2305.
18. Varech D., Jagues J., Bull. Soc. Chim. Fr., 1965, 67-70.
19. Ruzicka L., Muhr A. C., Helv. Chim. Acta, 27, 503-512 (1944).
20. Shoppee C. W., Jenkins R. H., Summers G. H. R., J. Chem. Soc., 1958, 3048-3058.
21. Denny W. A., Kumar V., Meakins G. D., Pragnell J., Wicha J., J. Chem. Soc., Perkin Trans. 1, 1972, 486-492.
22. Horiuchi C. A., Satoh J. Y., Synthesis, 1981, 312-314.