9(10→19)Abeo Steroids. Total Synthesis abeo-Estradiol, abeo-Estradiol 3-Methyl Ether, and 17α-Ethynyl abeo-Estradiol 3-Methyl Ether

Journal of Organic Chemistry

Volumn 41, Issue 9, 1976, Pages 1601-1603

  Abushanab, Elie ^a   Lee, Daw Yuan ^a   Meresak, William A ^a   Duax, William L ^b  

^a UNIVERSITY OF RHODE ISLAND   (United States)

^b HAUPTMAN WOODWARD MEDICAL RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; ESTRADIOL; ESTROGEN; ETHER DERIVATIVE; ETHINYLESTRADIOL; HORMONE; NORSTEROID;

ARTICLE; BIOLOGY; CONTRACEPTION; CONTRACEPTIVE AGENTS, ESTROGEN--ANALYSIS; CONTRACEPTIVE AGENTS, FEMALE--ANALYSIS; CONTRACEPTIVE AGENTS--ANALYSIS; ENDOCRINE SYSTEM; ESTRADIOL--ANALYSIS; ETHINYL ESTRADIOL--ANALYSIS; EXAMINATIONS AND DIAGNOSES; FAMILY PLANNING; LABORATORY EXAMINATIONS AND DIAGNOSES; LABORATORY PROCEDURES; PHYSIOLOGY; SYNTHESIS; TECHNIQUE; DRUG ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ESTRADIOL 3 METHYL ETHER DERIVATIVE; IN VITRO STUDY; INFRARED SPECTROMETRY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THEORETICAL STUDY; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY ANALYSIS;

BIOLOGY; CONTRACEPTION; CONTRACEPTIVE AGENTS, ESTROGEN--ANALYSIS; CONTRACEPTIVE AGENTS, FEMALE--ANALYSIS; CONTRACEPTIVE AGENTS--ANALYSIS; ENDOCRINE SYSTEM; ESTRADIOL--ANALYSIS; ESTROGENS; ETHINYL ESTRADIOL--ANALYSIS; EXAMINATIONS AND DIAGNOSES; FAMILY PLANNING; HORMONES; LABORATORY EXAMINATIONS AND DIAGNOSES; LABORATORY PROCEDURES; PHYSIOLOGY;

ESTRADIOL; ETHINYL ESTRADIOL; METHODS; METHYL ETHERS; NORSTEROIDS; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0017143406     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00871a026     Document Type: Article

References (15)

1. R. Doll and M. P. Vessey, Br. Med. Bull., 26, 33 (1970).
2. J. P. Bennett, “Chemical Contraception”, Columbia University Press, New York, N.Y. 1974, pp 101-107.
3. S. M. Kupchan and E. Abushanab, Tetrahedron Lett., 3075 (1965).
4. S. M. Kupchan, E. Abushanab, K. T. Shamasundar, and A. W. By, J. Am. Chem. Soc., 89, 6327 (1967).
5. F. Kohen, L. K. Lala, W. VanBever, and R. E. Counsell, Chem. Commun., 347 (1969).
6. F. Kohen, W. VanBever, and R. E. Counsell, J. Org. Chem., 35, 2272 (1970).
7. N. Cohen, B. L. Banner, W. F. Eichel, D. R. Parrish, G. Saucy, J. M. Cassal, W. Meier, and A. Furst, J. Org. Chem., 40, 681 (1975).
8. U. Eder, G. Haffer, J. Ruppert, G. Sauer, and R. Wiechert, German Offen. 2 253 088 (1974).
9. D. E. Bays, R. C. Cookson, and S. MacKenzie, J. Chem. Soc. B, 215 (1967).
10. W. E. Bachmann and J. Controulis, J. Am. Chem. Soc., 73, 2636 (1951).
11. E. J. Corey and G. W. J. Fleet, Tetrahedron Lett., 4499 (1973).
12. T. W. Huffman and P. G. Arapakos, J. Org. Chem., 30, 1604 (1965).
13. G. H. Douglas, J. M. H. Graves, D. Hartley, G. A. Hughs, B. J. McLoughlin, J. Sidall, and H. Smith, J. Chem. Soc., 5072 (1963).
14. G. T. DeTitta, J. W. Edmonds, D. A. Langs, and H. Hauptman, Acta Crystallogr., Sect. A, in press.
15. G. Germain, P. Main, and M. M. Woolfson, Acta Crystallogr., Sect. A, 27, 368 (1971).