Development of an efficient and stereoselective manufacturing route to idoxifene

Organic Process Research and Development

Volumn 5, Issue 5, 2001, Pages 479-490

  Ace, Karl W ^a   Armitage, Mark A ^a   Bellingham, Richard K ^a   Blackler, Paul D ^a   Ennis, David S ^a,b   Hussain, Nigel ^a   Lathbury, David C ^a,b   Morgan, David O ^a   O'Connor, Noah ^a   Oakes, Graham H ^a,c   Passey, Stephen C ^a,d   Powling, Laurence C ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c UNIVERSITY OF LIVERPOOL   (United Kingdom)

^d UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035537538     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0100394     Document Type: Article

References (34)

1. McCague, R. Br. Patent GB 2174088, 1986.
2. McCague, R.; Leclercq, G.; Legros, N.; Goodman, J.; Backburn, G. M.; Jarman, M.; Foster, A. B. J. Med. Chem. 1989, 32, 2527.
3. Rowlands, M. G.; Parr, I. B.; McCague, R.; Jarman, M.; Goddard, J. M. Biochem. Pharmacol. 1990, 40, 283.
4. Chander, S. K.; McCague, R.; Luqmani, Y.; Newton, C.; Dowsett, M.; Jarman, M.; Coombes, R. C. Cancer Res. 1991, 51, 5851.
5. Haynes, B. P.; Parr, I. B.; Griggs, L. J.; Jarman, M. Breast Cancer Res. Treat. 1991, 19, 174.
6. Hardcastle. I. R.; Rowlands, M. G.; Houghton, J.; Parr, I. R.; Potter, G. A.; Jarman, M. J. Med. Chem. 1995, 38, 241.
7. Hardcastle, I. R.; Rowlands, M. G.; Grimshaw, R. M.; Houghton, J.; Jarman, M.; Sharff, A.; Neidle, S. J. Med. Chem. 1996, 39, 999.
8. McCague, R.; Potter, G. A.; Jarman, M. Org. Prep. Proced. Int. 1994, 26(3), 343.
9. (a) Mukaiyama, T.; Sato, T.; Hanna, J. Chem. Lett. 1973, 1041.
10. (b) McMurry, J. E.; Fleming, M. P.; J. Am. Chem. Soc. 1974, 96, 4708.
11. (c) McMurry, J. E.; Fleming, M. P.; Kees, K. L.; Krepski, L. R. J. Org. Chem. 1978, 43, 3255.
12. (d) Robertson, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon: Oxford; 1991, p 563.
13. Ennis, D. S.; Lathbury, D. C.; Wanders, A.; Watts, D. Org. Process Res. Dev. 1998, 2(5), 287.
14. (a) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405.
15. (b) McMurry, J. E. Chem. Rev. 1989, 89, 1513.
16. Coe, P. L.; Scriven, C. E. J. Chem. Soc., Perkin Trans, 1 1986, 475.
17. (a) Shani, J.; Gazit, A.; Livshitz, T.; Biran, S. J. Med. Chem. 1985, 28, 1504.
18. (b) Schwartz, W.; Hartmann, R. W.; Schonenberger, H. Arch. Pharmacol. 1991, 324, 223.
19. (c) Gauthier, S.; Mailhot, J.; Labrie, F. J. Org. Chem. 1996, 61, 3890.
20. Nayak, S. K.; Banerji, A. J. Org. Chem. 1991, 56, 1940.
21. Reetz, M. T. In Organotitanium Reagents in Organic Synthesis; Springer Verlag: Berlin, 1986; p 21.
22. Cram, D. J.; Abd Elhafez, F. A. J. Am. Chem. Soc. 1952, 74, 5828.
23. (a) Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 9, 2199.
24. (b) Anh, N. T. Top. Curr. Chem. 1980, 88, 145.
25. Einhorn, J.; Einhorn, C.; Luche, J.-L. Synth. Commun. 1990, 20(8), 1105. 6). This procedure was used to prepare supplies of ketone 13 for laboratory-scale investigations on downstream chemistry.
26. Fadel, A.; Garcia-Argote, S. Tetrahedron: Asymmetry 1996, 7(4), 1159.
27. Robertson, D. W.; Katzenellenbogen, J. A. J. Org. Chem. 1982, 47, 2387.
28. Canonne, P.; Belley, M.; Fytas, G.; Plamondon, J. Can. J. Chem. 1988; 66, 168.
29. Poindexter, G. S.; Owens, D. A.; Dolan, P. L.; Woo, E. J. Org. Chem. 1992, 57, 7(23), 6257.
30. Cason J.; Baxter, W. M.; DeAcetis, W. J. Org. Chem. 1959, 24, 247.
31. Silverman, G. S.; Rakita, P. E. Handbook of Grignard Reagents; Marcel Dekker: New York, 1996; pp 53-78.
32. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman: Essex, 1989; pp 443-445.
33. McCague, R. J. Chem. Soc., Perkin Trans. 1 1987, 1011.
34. Bell, R. A.; Dickson. K. C.; Valliant, J. F. Can. J. Chem. 1999, 77, 146.