Synthesis of (±)-B(9a)-homo-C-nor-3-methoxy-12-oxa-17-vinyl-estra- 1,3,5(10)-trienes

Tetrahedron

Volumn 54, Issue 45, 1998, Pages 13805-13812

  Wilmouth, Serge ^a   Toupet, Loïc ^b   Pellissier, Hélène ^a   Santelli, Maurice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

^b UMR 6626   (France)

Author keywords

[No Author keywords available]

Indexed keywords

11,12 NOR 11,13 DIHYDROXY 3 METHOXY 17 VINYLESTRA 1,3,5(10) TRIENE; 11,9 (2 PROPYL) 3 METHOXY 12 OXA 17 VINYLESTRA 1,3,5(10) TRIENE; ALKADIENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ESTERIFICATION; PRIORITY JOURNAL; PYROLYSIS; STEREOCHEMISTRY; STEROIDOGENESIS; STRUCTURE ANALYSIS;

EID: 0032487950     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00850-3     Document Type: Article

References (20)

1. [1] Address X-ray correspondence to this author.
2. [2] (a) Ouvrard, P.; Tubul, A.; Santelli, M. Bull. Soc. Chim. Fr. 1993, 130, 772-778.
3. (b) Michellys, P.Y.; Pellissier, H.; Santelli, M. Tetrahedron Lett. 1993, 34, 1931-1934.
4. (c) Pellissier, H.; Santelli, M. Tetrahedron 1996, 52, 9093-9100.
5. [3] (a) Pellissier, H.; Wilmouth, S.; Santelli, M. Bull. Soc. Chim. Fr., 1995, 132, 627-641.
6. (b) Pellissier, H.; Wilmouth, S.; Santelli, M. Tetrahedron Lett., 1996, 37, 5107-5110.
7. [4] Kametani, T.; Nemoto, H.; Ishikawa, H.; Shiroyama, K.; Fukumoto, K. J. Am. Chem. Soc. 1976, 98, 3378-3379.
8. [5] Wilmouth, S.; Pellissier, H.; Santelli, M. Tetrahedron 1998, 54, 000.
9. 13C NMR spectrum is to reduce the intensity of the signal due to the carbon bearing the deuterium; for examples see: Brownstein, S.; Burton, G. W.; Hughes, L.; Ingold, K. U. J. Org. Chem. 1989, 54, 560-569.
10. [7] Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209-220 and 221-264.
11. [8] (a) Kirmse, W. Topics in Current Chemistry 1979, 80, 125-311.
12. (b) Vogel, P. Carbocation Chemistry; Elsevier: Amsterdam, 1985.
13. [9] (a) Concerning the bicyclo[3.3.0]octane, see: Eliel, E. L.; Allinger, N. L.; Angyal, S. J.; Morrison, G. A. Conformational Analysis, Interscience Publ.: New York, 1965, p. 227.
14. (b) Concerning the 2-oxabicyclo[3.3.0]octane, see: Prochazka, M.; Cerny, J. V.; Smisek, M. Collection Czech. Chem. Commun. 1966, 31, 1315-1322.
15. [10] (a) Kametani, T.; Kondoh, H.; Tsubuki, M.; Honda, T. J. Chem. Soc., Perkin Trans. 1 1990, 5-10.
16. (b) Kametani, T.; Matsumoto, H.; Honda, T.; Fukumoto, K. Tetrahedron Lett. 1981, 22, 2379-2380.
17. (c) Kametani, T.; Matsumoto, H.; Honda, T. Tetrahedron 1981, 37, 3813-3817.
18. [11] Pitt, C. G.; Rector, D. H.; White, D. H.; Wani, M. C.; McPhail, A. T.; Onan, K. D. J. Chem. Soc., Perkin Trans 1 1977, 1144-1150.
19. [12] (a) Pellissier, H.; Michellys, P. -Y.; Santelli, M. Tetrahedron 1997, 53, 7577-7586.
20. (b) Pellissier, H.; Michellys, P. -Y.; Santelli, M. Tetrahedron 1997, 53, 10733-10742.