Steroid-like ring skeletons by cyclohexadiene annulation to enamines with alkynylcarbene complexes of chromium and tungsten via pyran-2-ylidene complexes

Journal of the American Chemical Society

Volumn 118, Issue 44, 1996, Pages 10853-10861

  Aumann, Rudolf ^a   Meyer, Adam G ^a,b   Fröhlich, Roland ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

METAL COMPLEX;

ARTICLE; CATALYSIS; COMPLEX FORMATION; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STEROIDOGENESIS;

EID: 0029843633     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961020x     Document Type: Article

References (44)

1. Part 86: Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics, in press.
2. (a) Wulff, W. D.; Yang, D. J. Am. Chem. Soc. 1984, 106, 7565-7567.
3. (b) Wulff, W. D.; Tang, P.-C.; Chan, K.-S.; McCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813-5832.
4. (c) Faron, K. L.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 6419-6420.
5. (d) Pipoh, R.; von Eldik, R.; Wang, S. L. B.; Wulff, W. D. Organometallics 1992, 11, 490-492.
6. (e) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 19, 5531-5547.
7. (f) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 5, pp 1065-1113.
8. (a) Camps, F.; Moretó, J. M.; Ricart, S.; Viñas, J. M. Angew. Chem. 1991, 103, 1540-1542; Angew. Chem., Int. Ed. Engl. 1991, 1470-1471.
9. (a) Camps, F.; Moretó, J. M.; Ricart, S.; Viñas, J. M. Angew. Chem. 1991, 103, 1540-1542; Angew. Chem., Int. Ed. Engl. 1991, 1470-1471.
10. (b) Camps, F.; Moretó, J. M.; Ricart, S.; Viñas, J. M.; Molins, E.; Miravitlles, C. J. Chem. Soc., Chem. Commun. 1989, 1560-1562.
11. (c) Camps, F.; Jordi, L.; Moretó, J. M.; Ricart, S.; Castano, A. M.; Echavarren, A. M. J. Organomet. Chem. 1992, 436, 189-198.
12. (d) Segundo, A.; Moretó, J. M.; Vinas, J. M.; Ricart, S.; Molins, E. Organometallics 1994, 13, 2467-2471.
13. (e) Camps, F.; Llebaria, A.; Moretó, J. M.; Ricart, S.; Viñas, J. M. Tetrahedron Lett. 1990, 31, 2479-2482.
14. (f) Lluch, A.-M.; Jordi, L.; Sanchez-Baeza, F.; Ricart, S.; Camps, F.; Messeguer, A.; Moretõ, J. J. Tetrahedron Lett. 1992, 33, 3021-3022.
15. (g) Jordi, L.; Moretó, J. M.; Ricart, S.; Viñas, J. M.; Mejias, M.; Molins, E. Organometallics 1992, 11, 3507-3510.
16. (h) Jordi, L.; Segundo, A.; Camps, F.; Ricart, S.; Moretó, J. M. Organometallics 1993, 12, 3795-3797.
17. (i) Jordi, L.; Camps, F.; Ricart, S.; Vinas, J. M.; Moretó, J. M.; Mejias, M.; Molins, E. J. Organomet. Chem. 1995, 494, 53-64.
18. (j) Jordi, L.; Moretó, J. M.; Ricart, S.; Viñas, J. M.; Molins, E.; Miravitlles, C. J. Organomet. Chem. 1993, 444, C28-C30.
19. (k) Jordi, L.; Camps, F.; Ricart, S.; Viñas, J. M.; Moretó, J. M.; Mejias, M.; Molins, E. J. Organomet. Chem. 1995, 494, 53-64.
20. de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32.
21. (a) Aumann, R.; Roths, K.; Grehl, M. Synlett 1993, 669-671.
22. (b) Aumann, R.; Kössmeier, M.; Roths, K.; Fröhlich, R. Synlett 1994, 1041-1044.
23. (c) Aumann, R.; Roths, K.; Läge, M.; Krebs, B. Synlett 1993, 667-669.
24. (d) Meyer, A. G.; Aumann, R. Synlett 1995, 1011-1013.
25. Barluenga, J.; Aznar, F.; Barluenga, S. J. Chem. Soc., Chem. Commun. 1995, 1973-1974.
26. (a) Aumann, R.; Heinen, P.; Hinterding, P.; Sträter. N.; Krebs, B. Chem. Ber. 1991, 124, 1229-1236.
27. (b) Aumann, R.; Heinen, H.; Dartmann, M.; Krebs, B. Chem. Ber. 1991, 124, 2343-2347.
28. Aumann, R.; Roths, K.; Jasper, B.; Fröhlich, R. Organometallics 1996, 15, 1257-1264.
29. Wang, S. L.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 4550-4552.
30. (a) Rees, C. W.; von Angerer, E. J. Chem. Soc., Chem. Commun. 1972, 420.
31. (b) Gilchrist, T. L.; Livingstone, R.; Rees, C. W.; von Angerer, E. J. Chem. Soc., Perkin Trans. 1 1973, 2535-2539.
32. Berke, H.; Härter, P.; Huttner, G.; Zsolnai, L. Z. Naturforsch. 1981, 36b, 929-937.
33. Aumann, R.; Heinen, H. Chem. Ber. 1987, 120, 537-540.
34. Juneau, K. N.; Hegedus, L. S.; Roepke, F. W. J. Am. Chem. Soc. 1989, 111, 4762-4765.
35. Licandro, E.; Maiorana, S.; Papagni, A.; Zanotti Gerosa, A.; Cariati, F.; Bruni, S.; Moret, M.; Chiesi Villa, A. Inorg. Chim. Acta 1994, 220, 233-247.
36. (a) Adams, R. D.; Chen, L. J. Am. Chem. Soc. 1994, 116, 4467-4468.
37. (b) Adams, R. D.; Chen, L.; Huang, M. Organometallics 1994, 13, 2696-2705.
38. Garlaschelli, L.; Malatesta, M. C.; Panzeri, S.; Albinati, A.; Ganazzoli, F. Organometallics 1987, 6, 63-72.
39. Mills, O. S.; Redhouse, A. D. Angew. Chem. 1965, 77, 1142; Angew. Chem., Int. Ed. Engl. 1965, 4, 1082.
40. Mills, O. S.; Redhouse, A. D. Angew. Chem. 1965, 77, 1142; Angew. Chem., Int. Ed. Engl. 1965, 4, 1082.
41. For numbering of atoms see Figures 1 and 2, respectively. Numbering is different from that numbering according to the IUPAC rules.
42. For similar effects, see: Aumann, R.; Hinterding, P. Chem. Ber. 1992, 125, 2765-2772.
43. Pancrazi, A.; Khuong-Huu, Q. Tetrahedron 1974, 30, 2337-2343.
44. Roths, K. Dissertation, Münster, 1996.