Enantioselective synthesis and photoracemization studies of (±)-2- cyclopropyl-7,8-dimethoxy-2H-chromene-5-carboxylic acid methyl ester, an advanced intermediate of a dihydrofolate reductase inhibitor

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5321-5324

  Wipf, Peter ^a   Weiner, Warren S ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOPROPYL 7,8 DIMETHOXY 2H CHROMENE 5 CARBOXYLIC ACID METHYL ESTER; CHROMENE DERIVATIVE; COTRIMOXAZOLE; DIHYDROFOLATE REDUCTASE INHIBITOR; PHENOL DERIVATIVE; SULFONAMIDE; TRIMETHOPRIM; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BRONCHITIS; ENZYME INHIBITION; METHODOLOGY; PNEUMONIA; PSEUDOMONAS; STAPHYLOCOCCUS AUREUS; SYNTHESIS; URINARY TRACT INFECTION;

EID: 0033063994     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990352s     Document Type: Article

References (35)

1. Balasubramanian, B. N.; Kadow, J. F.; Kramer, R. A.; Vyas, D. M. Annu. Rep. Med. Chem. 1998, 33, 151.
2. McCormack, J. J. In Comprehensive Medicinal Chemistry; Sammes, P. G., Taylor, J. B., Eds.; Pergamon: Oxford 1990; Vol. 2, Chapter 7.2, p 271.
3. Masciadri, R. U.S. Patent 5,773,446; Hoffmann-La Roche, June 30, 1998.
4. Masciadri, R. U.S. Patent 5,773,446; Hoffmann-La Roche, June 30, 1998.
5. (a) Harrity, J. P. A.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488.
6. (b) Chang, S.; Grubbs, R. H. J. Org. Chem. 1998, 63, 864.
7. (c) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343.
8. (d) Johannes, C. W.; Visser, M. S.; Weatherhead, G. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 8340.
9. For the use of kinetic resolution or chromatographic separation of chiral chromenes, see: (a) Vander Velde, S. L.; Jacobsen, E. N. J. Org. Chem. 1995, 60, 5380. (b) Loncartomaskovic, L.; Mintas, M.; Trotsch, T.; Mannschreck, A Enantiomer 1997, 2, 459. Chiral chromene was also obtained from dehydrogenation of chromane and cyclization of an α,β-unsaturated sulfoxide: (c) Stocker, A.; Netscher, T.; Rüttimann, A.; Müller, R. K.; Schneider, H.; Todaro, L. J.; Derungs, G.; Woggon, W.-D. Helv. Chim. Acta 1994, 77, 1721. (d) Solladie, G.; Moine, G. J. Am. Chem. Soc. 1984, 106, 6097.
10. For the use of kinetic resolution or chromatographic separation of chiral chromenes, see: (a) Vander Velde, S. L.; Jacobsen, E. N. J. Org. Chem. 1995, 60, 5380. (b) Loncartomaskovic, L.; Mintas, M.; Trotsch, T.; Mannschreck, A Enantiomer 1997, 2, 459. Chiral chromene was also obtained from dehydrogenation of chromane and cyclization of an α,β-unsaturated sulfoxide: (c) Stocker, A.; Netscher, T.; Rüttimann, A.; Müller, R. K.; Schneider, H.; Todaro, L. J.; Derungs, G.; Woggon, W.-D. Helv. Chim. Acta 1994, 77, 1721. (d) Solladie, G.; Moine, G. J. Am. Chem. Soc. 1984, 106, 6097.
11. For the use of kinetic resolution or chromatographic separation of chiral chromenes, see: (a) Vander Velde, S. L.; Jacobsen, E. N. J. Org. Chem. 1995, 60, 5380. (b) Loncartomaskovic, L.; Mintas, M.; Trotsch, T.; Mannschreck, A Enantiomer 1997, 2, 459. Chiral chromene was also obtained from dehydrogenation of chromane and cyclization of an α,β-unsaturated sulfoxide: (c) Stocker, A.; Netscher, T.; Rüttimann, A.; Müller, R. K.; Schneider, H.; Todaro, L. J.; Derungs, G.; Woggon, W.-D. Helv. Chim. Acta 1994, 77, 1721. (d) Solladie, G.; Moine, G. J. Am. Chem. Soc. 1984, 106, 6097.
12. For the use of kinetic resolution or chromatographic separation of chiral chromenes, see: (a) Vander Velde, S. L.; Jacobsen, E. N. J. Org. Chem. 1995, 60, 5380. (b) Loncartomaskovic, L.; Mintas, M.; Trotsch, T.; Mannschreck, A Enantiomer 1997, 2, 459. Chiral chromene was also obtained from dehydrogenation of chromane and cyclization of an α,β-unsaturated sulfoxide: (c) Stocker, A.; Netscher, T.; Rüttimann, A.; Müller, R. K.; Schneider, H.; Todaro, L. J.; Derungs, G.; Woggon, W.-D. Helv. Chim. Acta 1994, 77, 1721. (d) Solladie, G.; Moine, G. J. Am. Chem. Soc. 1984, 106, 6097.
13. Tanaka, M.; Ikeya, Y.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Tetrahedron 1995, 51, 11703.
14. Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 127.
15. Richter, L. S.; Gadek, T. R. Tetrahedron Lett. 1994, 35, 4705.
16. (a) Walton, D. R. M.; Waugh, F. J. Organomet. Chem. 1972, 37, 45.
17. (b) Birkofer, L.; Ritter, A.; Uhlenbrauck, H. Chem. Ber. 1963, 96, 3280.
18. (a) Parker, K. A.; Ledeboer, M. W. J. Org. Chem. 1996, 61, 3214.
19. (b) Helal, C. J.; Magriotis, P. A.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 10938.
20. 2 in the presence of catalytic DMF: Thayer, F. K. Organic Syntheses; Gilman, H., Ed.; Wiley: New York, 1932; Coll. Vol. 1, p 12.
21. (a) Silbert, L. S.; Foglia, T. A. Anal. Chem. 1985, 57, 1404.
22. (b) Cannon, J. G.; Darko, L. L. J. Org. Chem. 1964, 29, 3419.
23. (c) Bur, D.; Luyten, M. A.; Wynn, H.; Provencher, L. R.; Jones, J. B.; Gold, M.; Friesen, J. D.; Clarke, A. R.; Holbrook, J. J. Can. J. Chem. 1989, 67, 1065.
24. 10a
25. (a) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130.
26. (b) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651.
27. (a) Ishibashi, M.; Ohizumi, Y.; Cheng, J.; Nakamura, H.; Hirata, Y.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1988, 53, 2855.
28. 254 +8600) due to the styrene chromophore, indicative of a left-handed helix. The cyclopropyl side chain of 2 adopts a pseudoequatorial position and thus the absolute configuration of 2 is S. (Illustration presented)
29. Van Gemert, B. In Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R. J., Eds.; Plenum: New York 1999; Vol. 1, Chapter 3, p 111.
30. Harie, G.; Samat, A.; Guglielmetti, R.; Van Parys, I.; Saeyens, W.; De Keukeleire, D.; Lorenz, K.; Mannschreck, A. Helv. Chim. Acta 1997, 80, 1122.
31. See, for example: Loncar, L.; Otocan, K.; Mintas, M.; Trötsch, T.; Mannschreck, A. Croat. Chem. Acta 1999, 66, 209.
32. (a) Venkateswarlu, Y.; Faulkner, D. J.; Steiner, J. L. R.; Corcoran, E.; Clardy, J. J. Org. Chem. 1991, 56, 6271.
33. (b) Jaipetch, T.; Kanghae, S.; Pancharoen, O.; Patrick, V. A.; Reutrakul, V.; Tuntiwachwuttikul, P.; White, A. H. Aust. J. Chem. 1982, 35, 351.
34. (c) Hamann, M. T.; Scheuer, P. J.; Kelly-Borges, M. J. Org. Chem. 1893, 58, 6565.
35. Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1997, 38, 7511.