Efficient oxidizing methods for the synthesis of oxandrolone intermediates

Chemical and Pharmaceutical Bulletin

Volumn 52, Issue 8, 2004, Pages 989-991

  Ginotra, Sandeep K ^a   Chhikara, Bhupender S ^a   Singh, Manish ^a   Chandra, Ramesh ^a   Tandon, Vibha ^a  

^a UNIVERSITY OF DELHI   (India)

Author keywords

2 iodoxy benzoic acid (IBX); Dehydrogenation; Hydrogenperoxide; NaOCl; Oxidation; Steroid

Indexed keywords

17ALPHA METHYLANDROSTAN 3BETA 17BETA DIOL; 17BETA HYDROXY 17ALPHA METHYL DELTA1 ANDROSTEN 3 ONE; 2 IODOXY BENZOIC ACID; BENZOIC ACID DERIVATIVE; DIMETHYL SULFOXIDE; HYPOCHLORITE SODIUM; MESTANOLONE; OXANDROLONE; UNCLASSIFIED DRUG; ANDROSTANEDIOL; ANDROSTANOLONE; BENZOIC ACID; CHLORINE; DRUG DERIVATIVE; IODINE;

ARTICLE; CHEMICAL REACTION; DRUG OXIDATION; DRUG SYNTHESIS; TEMPERATURE; CHEMICAL MODEL; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ANDROSTANE-3,17-DIOL; BENZOIC ACID; CHLORINE; DIHYDROTESTOSTERONE; IODINE; MODELS, CHEMICAL; OXANDROLONE; OXIDATION-REDUCTION; SODIUM HYPOCHLORITE;

EID: 16644401533     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.52.989     Document Type: Article

References (19)

1. Ritzén E. M., Nilsson O., Grigelioniene G., Holst M., Savendahl L., Wroblewski J., J. Steroid Biochem. Mol. Bio., 74, 383-386 (2000).
2. Ganag F. W., "Review of Medical Physiology," Prentice Hall International (UK) Ltd., London, 1991, pp. 335-359.
3. Osborne C. K., Yochmowitz M. G., Knight W. A., McGuire W. L., Cancer, 46, 2884-2888 (1980).
4. Pappo R., Jung J. C., Tetrahedron Lett., 3, 365-371 (1962).
5. Desai S. R., Ray D. W., Sayed Y. A., U.S. Patent 03-0109721 (2003).
6. Cabaj J. E., Kairys D. L., Zizelman P. M., PCT Int. Appl., Patent WO 02-100881 (2002).
7. Counsell R. E., Klimstra P. D., Colten F. B., J. Org. Chem., 27, 248-253 (1962).
8. Stang P. J., J. Org. Chem., 68, 2997-3008 (2003).
9. Stang P. J., Zhdankin V. V., Chem. Rev., 96, 1123-1178 (1996).
10. Zhdankin V. V., Stang P. J., Chem. Rev., 102, 2523-2584 (2002).
11. Varvolglis A., "Hypervalent Iodine in Organic Synthesis," Academic Press, San Diego, 1997.
12. Ochiai M., "Chemistry in Hypervalent Compounds," Chap. 12, ed. by Akiba K. Y., Wiley-VCH, New York, 1999.
13. More J. D., Finney N. S., Org. Lett., 4, 3001-3003 (2002).
14. Nicolaou K. C., Zhong Y. L., Baran P. S., Angew. Chem. Int. Ed., 39, 625-628 (2000).
15. Noyori R., Aoki M., Sato K., Chem. Commun., 16, 1977-1986 (2003).
16. Dess D. B., Martin J. C., J. Am. Chem. Soc., 113, 7277-7287 (1991).
17. "Elsevier Encyclopaedia of Organic Chemistry," Vol. 14 S Part 3, p. 2024S.
18. Shi J. D., Huang R. Q., Zhongguo Yiyao Gongye Zazhi, 29, 422-423 (1998).
19. Lee G. A., Freedman H. H., Tetrahedron Lett., 17, 1641-1644 (1976).