Synthesis of a C, D ring analog of 17-α-hydroxyprogesterone

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6127-6130

  Schweiger, Edwin J ^a   Joullié, Madeleine M ^b   Weisz, Paul B ^c  

^a SIBIA Corp   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

^c UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYPROGESTERONE; PROGESTERONE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROPHILICITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030842435     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01389-0     Document Type: Article

References (22)

1. Folkman, J.; Langer, R.; Linhardt, C.; Haudenschild, C.; Taylor, S. Science 1983, 221, 719-725.
2. Rodén, L.; Ananth, S.; Campbell, P.; Curenton, T.; Ekborg, G.; Manzella, S.; Pillion, D.; Meezan, E. In Heparin and Related Polysaccharides; D. A. Lane, I. Björk and U. Lindahl, Eds.; Plenum Press: New York, 1992; Vol. 313; 1-20.
3. Crum, R.; Szabo, S.; Folkman, J. Science 1985, 230, 1375-1378.
4. Hajos, Z. G.; Parrish, D. R. In Organic Syntheses 1985; Vol. 63; 26-36.
5. Barton, D. H. R.; Motherwell, W. B.; Zard, S. Z. J. Chem. Soc., Chem. Commun. 1981, 774-775.
6. Biollaz, M.; Haefliger, W.; Velarde, E.; Crabbé, P.; Fried, J. H. J. Chem. Soc., Chem. Commun. 1971, 1322-1323.
7. Bose, A. K.; Dahill, R. T. J. Tetrahedron Lett. 1963, 15, 959-963.
8. Clase, J. A.; Money, T. J. Chem Soc., Chem. Commun. 1990, 1503-1504.
9. Nédélec, L.; Torelli, V.; Hardy, M. J. Chem. Soc., Chem. Commun. 1981, 775-777.
10. Nitta, I.; Fujimori, S.; Ueno, H. Bull. Chem. Soc. Jpn. 1985, 58, 978-980.
11. Schneider, W. P.; Hanze, A. R. In 2,769,823; The Upjohn Company: United States Patent, 1956,.
12. Johnson, W. S. J. Am. Chem. Soc. 1944, 66, 215-217.
13. Bauduin, G.; Pietrasanta, Y. Tetrahedron 1973, 29, 4225-4231.
14. Raggio, M. L.; Watt, D. S. J. Org. Chem. 1976, 41, 1873-1875.
15. Bauduin, G.; Pietrasanta, Y. C. R. Acad. Sci., Ser. C 1973, 277, 53-55.
16. Bauduin, G.; Bondon, D.; Pietrasanta, Y.; Pucci, B. Tetrahedron 1980, 36, 245-253.
17. Micheli, R. A.; Hajos, Z. G.; Cohen, N.; Parrish, D. R.; Portland, L. A.; Sciamanna, W.; Scott, M. A.; Wehrli, P. A. J. Org. Chem. 1975, 40, 675-681.
18. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1973, 38, 3239-3243.
19. Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
20. Fieser, L. F.; Fieser, M. In Reagents for Organic SynthesisJohn Wiley and Sons: New York, 1967; Vol. 1; 729.
21. Bhacca, N. S.; Gurst, J. E.; Williams, D. H. J. Am. Chem. Soc. 1965, 87, 302-305.
22. Folkman, J., Department of Surgery and Department of Anatomy and Cellular Biology, Harvard Medical School, personal communication, 1992.