Synthesis of novel steroid backbones via photoinduced electron transfer initiated domino cyclizations of silyl enol ethers

Synthesis

Volumn , Issue 4, 2004, Pages 619-633

  Bunte, Jens O ^a   Rinne, Stefanie ^a   Mattay, Jochen ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

Cyclizations; Domino reactions; Electron transfer; Stereoselectivity; Steroids

Indexed keywords

POSITIVE IONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CYCLIZATION PROCESS; STEROID COMPOUNDS;

ETHERS;

CATION; ETHER DERIVATIVE; RADICAL; SILYL ENOL ETHER DERIVATIVE; STEROID; UNCLASSIFIED DRUG;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ELECTRON TRANSPORT; PHOTOCHEMISTRY; PHOTOINDUCED ELECTRON TRANSFER; REACTION ANALYSIS; REVIEW; RING CLOSING METATHESIS; STEREOCHEMISTRY; STEROIDOGENESIS; SYNTHESIS; TECHNIQUE;

EID: 1642343328     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815956     Document Type: Review

References (47)

1. (a) Robinson, R. J. Chem. Soc. 1917, 762.
2. (b) Robinson, R. J. Chem. Soc. 1917, 867.
3. (c) Schöpf, C.; Lehmann, G.; Arnold, W. Angew. Chem. 1937, 50, 779.
4. (a) Tietze, L. F.; Beifuss, U. Angew. Chem. Int. Ed. 1993, 32, 131; Angew. Chem. 1993, 105, 137;.
5. (a) Tietze, L. F.; Beifuss, U. Angew. Chem. Int. Ed. 1993, 32, 131; Angew. Chem. 1993, 105, 137;.
6. (b)Tietze, L. F. Chem. Rev. 1996, 96, 136.
7. (c) Malacria, M. Chem. Rev. 1996, 96, 306.
8. (d) Hudlicky, T. Chem. Rev. 1996, 96, 3.
9. (a) Curran, D. P. Synthesis 1988, 417.
10. (b) Curran, D. P. Synthesis 1988, 489.
11. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
12. (d) McCarroll, A. J.; Walton, J. C. Angew. Chem. Int. Ed. 2001, 40, 2224; Angew. Chem. 2001, 113, 2282.
13. (d) McCarroll, A. J.; Walton, J. C. Angew. Chem. Int. Ed. 2001, 40, 2224; Angew. Chem. 2001, 113, 2282.
14. (a) Baguley, P. A.; Walton, J. C. Angew. Chem. Int. Ed. 1998, 37, 3072; Angew. Chem. 1998, 110, 3272.
15. (a) Baguley, P. A.; Walton, J. C. Angew. Chem. Int. Ed. 1998, 37, 3072; Angew. Chem. 1998, 110, 3272.
16. (b) Snider, B. B. Chem. Rev. 1996, 96, 339.
17. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
18. (a) Kovarnos, G. J.; Turro, N. J. Chem. Rev. 1986, 86, 401.
19. (b) Mattay, J.; Vondenhof, M. Top. Curr. Chem. 1991, 159, 219.
20. (c) Kovarnos, G. J. Fundamentals of Photoinduced Electron Transfer; VCH Publishers: New York, 1993.
21. (d) Electron Transfer in Chemistry, Vol. 1 and 2; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001.
22. (e) Heinemann, C.; Demuth, M. J. Am. Chem. Soc. 1999, 121, 4894.
23. (f) Hintz, S.; Heidbreder, A.; Mattay, J. Top. Curr. Chem. 1996, 177, 77.
24. (g) Oelgemöller, M.; Bunte, J. O.; Mattay, J. In Synthetic Organic Photochemistry; Ramamurthy, V.; Schanze, K., Eds.; Marcel & Dekker: New York, in press.
25. Bunte, J. O.; Mattay, J. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd Ed.; Horspool, W. M.; Lenci, F., Eds.; CRC Press: Boca Raton, 2004, Chap. 10.
26. (a) Ackermann, L.; Heidbreder, A.; Wurche, F.; Klärner, F.-G.; Mattay, J. J. Chem. Soc., Perkin Trans. 2 1999, 863.
27. (b) Hintz, S.; Mattay, J.; van Eldik, R.; Fu, W.-F. Eur. J. Org. Chem. 1998, 1583.
28. (c) Bunte, J. O.; Rinne, S.; Schäfer, C.; Neumann, B.; Stammler, H.-G.; Mattay, J. Tetrahedron Lett. 2003, 45.
29. Boehm, H. M.; Handa, S.; Pattenden, G.; Roberts, L.; Blake, A. J.; Li, W. S. J. Chem. Soc., Perkin Trans. 1 2000, 3522.
30. Buchecker, R.; Marti, U.; Eugster, C. H. Helv. Chim. Acta 1982, 65, 896.
31. (a) Johnson, W. S.; Bartlett, W. R.; Czeskis, B. A.; Gautier, A.; Lee, C. H.; Lemoine, R.; Leopold, E. J.; Luedtke, G. R.; Bancroft, K. J. J. Org. Chem. 1999, 64, 9587.
32. (b) Brady, S. F.; Ilton, M. A.; Johnson, W. S. J. Am. Chem. Soc. 1968, 90, 2882.
33. (a) Barco, A.; Benetti, S.; Pollini, G. P. Synthesis 1973, 316.
34. (b) De Silva, A. N.; Francis, C. L.; Ward, A. D. Aust. J. Chem. 1993, 46, 1657.
35. (a) Imamoto, T. Comprehensive Organic Synthesis - Organocerium Reagents, Vol. 1; Trost, B. M.; Fleming, I.; Schreiber, S. L., Eds.; Pergamon Press: Oxford, 1991, 231.
36. (b) Takeda, N.; Imamoto, T. Org. Synth. 1999, 76, 228.
37. (c) Panev, S.; Dimitrov, V. Tetrahedron: Asymmetry 2000, 11, 1517.
38. Bergdahl, M.; Eriksson, M.; Nilsson, M.; Olsson, T. J. Org. Chem. 1993, 58, 7238.
39. Bunte, J. O. PhD thesis; Universität Bielefeld: Germany, 2003.
40. Webster, F. X.; Silverstein, R. M. Synthesis 1987, 922.
41. (a) Johnstone, R. A. W.; Rose, M. E. Tetrahedron 1979, 35, 2169.
42. (b) Giuliano, R. M.; Jordan, A. D. Jr.; Gauthier, A. D.; Hoogsteen, K. J. Org. Chem. 1993, 58, 4979.
43. (a) Kikani, B. B.; McKee, J. T.; Zanger, M. Synthesis 1990, 176.
44. (b) Campaigne, E.; Selby, T. P. J. Heterocycl. Chem. 1980, 17, 1255.
45. (c) Fuchs, R.; McGarrity, J. F. Synthesis 1992, 373.
46. (d) Duc, L.; McGarrity, J. F.; Meul, T.; Warm, A. Synthesis 1992, 391.
47. Armarego, W. L. F.; Perrin, D. D. In Purification of Laboratory Chemicals, 4th Ed.; Butterworth-Heinemann: Oxford, 1996.