Stereoselective approach to some novel 16-methylated and 16-halomethylated tetrahydropyran and δ-lactone derivatives in both the normal and the 13α-estrone series

Synlett

Volumn , Issue 11, 2002, Pages 1803-1806

  Frank, Éva ^a   Mernyák, Erzsébet ^a   Wölfling, János ^a   Schneider, Gyula ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

Author keywords

Cyclizations; Diastereoselectivity; Esterification; Estrone derivatives; Etherification

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ESTRONE DERIVATIVE; ETHER DERIVATIVE; GAMMA LACTONE DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; MOLECULAR INTERACTION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036420109     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34947     Document Type: Article

References (37)

1. (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
2. (b) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683.
3. (c) Tietze, L. F.; Schneider, C. J. Org. Chem. 1991, 56, 2476.
4. (d) Nakata, T.; Nomura, S.; Matsukura, H. Tetrahedron Lett. 1996, 37, 213.
5. (a) Alder, K.; Söll, H.; Söll, H. Liebigs Ann. Chem. 1949, 565, 73.
6. (b) Zoretic, P. A.: Yu, B.-C.; Biggers, M. S.; Caspar, M. L. J. Org. Chem. 1990, 3954.
7. (c) Espada, A.; Rodriguez, J.; Villaverde, M. C.; Riguera, R. Can. J. Chem. 1990, 68, 2039.
8. (d) Carr, G.; Dean, C.; Whittaker, D. J. Chem. Soc., Perkin Trans. 2 1988, 351.
9. (e) Narjes, F.; Schaumann, E. Liebigs Ann. Chem. 1993, 841.
10. (f) Yanamura, S.; Shizuri, Y.; Shigemori, H.; Okuno, Y.; Ohkubo, M. Tetrahedron 1991, 47, 635.
11. (a) Brown, H. C.; Lynch, G. J. J. Org. Chem. 1981, 46, 531.
12. (b) Kang, S. H.; Lee, J. H.; Lee, S. B. Tetrahedron Lett. 1998, 39, 59.
13. (a) Ishihara, J.; Nonaka, R.; Terasawa, Y.; Shiraki, R.; Yabu, K.; Kataoka, H.; Ochiai, Y.; Tadano, K. Tetrahedron Lett. 1997, 38, 8311.
14. (b) Nemoto, H.; Miyata, J.; Ihara, M. Tetrahedron Lett. 1999, 40, 1933.
15. (c) Miyata, J.; Nemoto, H.; Ihara, M. J. Org. Chem. 2000, 65, 504.
16. (d) Okimoto, Y.; Kikuchi, D.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2000, 41, 10223.
17. (e) Guindon, Y.; Guerin, B.; Chabot, C.; Ogilvie, W. J. Am. Chem. Soc. 1996, 118, 12528.
18. (a) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475.
19. (b) Rood, G. A.; DeeHaan, J. M.; Zibuck, R. Tetrahedron Lett. 1996, 37, 157.
20. (c) Clerici, F.; Gelmi, M. L.; Gambini, A.; Nava, D. Tetrahedron 2001, 57, 6429.
21. (d) Greeves, N.; Lee, W.-M.; Barkley, J. V. Tetrahedron Lett. 1997, 38, 6453.
22. Neverov, A. A.; Brown, R. S. J. Org. Chem. 1996, 61, 962.
23. (a) Baran, J. S. J. Med. Chem. 1967, 10, 1039.
24. (b) Ryzhenkov, V. E.; Prokopjev, A. A.; Nersisian, G. G.; Kameneva, I.; Shavva, A. G. Vopr. Med. Khim. 1987, 33, 65.
25. (c) Kameneva, I.; Shavva, A. G.; Losovskii, V. T.; Ryzhenkov, V. E. Biull. Eksp. Biol. Med. 1994, 117, 262.
26. Longcope, C.; Arunachalam, T.; Rafkind, I.; Caspi, E. Adv. Exp. Med. Biol. 1981, 138, 191.
27. (a) Tietze, L. F.; Schneider, G.; Wölfling, J.; Nöbel, T.; Wulff, C.; Schubert, I.; Rübeling, A. Angew. Chem. Int. Ed. 1998, 37, 2469; Angew. Chem. 1998, 110, 2644.
28. (a) Tietze, L. F.; Schneider, G.; Wölfling, J.; Nöbel, T.; Wulff, C.; Schubert, I.; Rübeling, A. Angew. Chem. Int. Ed. 1998, 37, 2469; Angew. Chem. 1998, 110, 2644.
29. (b) Tietze, L. F.; Schneider, G.; Wölfling, J.; Fecher, A.; Nöbel, T.; Petersen, S.; Schuberth, I.; Wulff, C. Chem.-Eur. J. 2000, 6, 3755.
30. (a) Schneider, G.; Bottka, S.; Hackler, L.; Wölfling, J.; Sohár, P. Liebigs Ann. Chem. 1989, 263.
31. (b) Mernyák, E.; Wölfling, J.; Bunkóczi, G.; Luo, L.; Schneider, T. R.; Schneider, G. Collect. Czech. Chem. Commun., in preparation.
32. 2. The compounds give correct elemental analyses.
33. Gosselin, P.; Perrotin, A.; Mille, S. Tetrahedron 2001, 57, 733.
34. Schönecker, B.; Lange, C.; Kötteritzsch, M.; Günther, W.; Weston, J.; Anders, E.; Görls, H. J. Org. Chem. 2000, 65, 5487.
35. (a) Frank,; Mernyák, E.; Wölfling, J.; Schneider, G. Synlett 2002, 419.
36. (b) Mernyák, E.; Lange, C.; Kötteritzsch, M.; Schönecker, B.; Görls, H.; Wölfling, J.; Schneider, G. Steroids 2002, in press.
37. (c) Schwarz, S.; Schönecker, B.; Fritsche, K.; Poser, A.; Lange, C.; Günther, W.; Göttke, S.; Görls, H.; Bäsler, S. Steroids 2002, in press.