New retinoid analogs from δ-pyronene, a natural synthon

European Journal of Organic Chemistry

Volumn , Issue 6, 1999, Pages 1489-1494

  Lambertin, Frédéric ^a   Wende, Martin ^a   Quirin, Marie Jeanne ^a   Taran, Martine ^a   Delmond, Bernard ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

Retinoids; Terpenoids; Wittig reactions; Pyronene

Indexed keywords

PYRONE DERIVATIVE; RETINOID DERIVATIVE; TERPENOID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032793499     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199906)1999:6<1489::AID-EJOC1489>3.0.CO;2-1     Document Type: Article

References (51)

1. D. Serramedan, F. Marc, M. Pereyre, C. Filliatre, P. Chabardes, B. Delmond, Tetrahedron Lett. 1992, 33, 4457-4460.
2. F. Marc, B. Soulet, D. Serramedan, B. Delmond, Tetrahedron 1994, 50, 3381-3388.
3. M. J. Quirin, M. Taran, B. Delmond, Can. J. Chem. 1996, 74, 1852-1856.
4. B. Boulin, B. Arreguy-San Miguel, B. Delmond, Tetrahedron 1998, 54, 2753-2762.
5. M. J. Quirin, M. Taran, B. Delmond, Svnth. Commun. 1995, 25, 3339-3345.
6. For general monographs, see: [6a] M. B. Sporn, A. B. Roberts, D. S. Goodman (Eds.), The Retinoids, vol. 1 and 2, Academic Press, Orlando, 1984.
7. [6b] M. B. Sporn, A. B. Roberts, D. S. Goodman (Eds.), The Retinoids: Biology, Chemistry and Medicine, 2nd ed., Raven Press, New York, 1994.
8. [6c] M. I. Dawson, W. H. Okamura (Eds.), Chemistry and Biology of Synthetic Retinoids, CRC Press, Boca Raton, 1990.
9. [6d] L. Packer (Ed.), Methods in Enzymology, Academic Press, New York, 1990, vol.89, part A.
10. [6e] L. Packer (Ed.), Methods in Enzymology, Academic Press, New York, 1991, vol. 90, part B.
11. By analogy with usual retinoids, these new derivatives were named "wo"-retinoids. With the taken numbering scheme, the systematic name for "iso"-retinal 7 is thus (all-E)-3,7-dimethyl-9-(2′,3′,3′-trimethyl-1′- cyclohexen-1′-yl)-2,4,6,8-nonatetraen-1-al.
12. For a review on utilizations of Wittig and related reactions in natural products synthesis, see: [8a] H. Pommer, P. C. Thieme, Top. Curr. Chem. 1983, 709, 165-188.
13. [8b] B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863-927.
14. [8c] E. Vedejs, M. J. Peterson, Top. Stereochem. 1994, 21, 1-157.
15. [8d] K. C. Nicolaou, M. W. Harter, J. L. Gunzner, A. Nadin, Liebigs Ann. 1997, 1283-1301.
16. [8e] W. S. Wadsworth, Org. React. 1977, 25, 73-253.
17. P. J. R. Nederlof, M. T. Moolenaar, E. R. De Waard, H. O. Huisman, Tetrahedron 1977, 33, 579-580.
18. [10a] W. Oroshnik, A. D. Mebane, J. Am. Chem. Soc. 1949, 71, 2062-2065.
19. [10b] H. Pommer, Angew. Chem. 1960. 72, 811-819.
20. [10c] M. Julia, D. Arnould, Bull. Soc. Chim. Fr. 1973, 746-750.
21. [10d] H. Pommer, A. Nurrenbach, Pure Appl. Chem. 1975, 43, 527-551.
22. [10e] S. M. Makin, Pure Appl. Chem. 1976, 47, 173-181.
23. [10f] G. L. Olson, H. C. Cheung, K. D. Morgan, C. Neukom, G. Saucy, J. Org. Chem. 1976, 41, 3287-3293.
24. [10g] P. S. Manchand, M. Rosenberger, G. Saucy, P. A. Wehrli, H. Wong, L. Chambers, M. P. Ferro, W. Jackson, Helv. Chim. Acta 1976, 59, 387-396.
25. [10h] P. S. Manchand, H. Wong, J.F. Blount, J .Org. Chem. 1978, 43, 4769-4774.
26. [10i] D. Arnould, P. Chabardes, G. Farge, M. Julia, Bull. Soc. Chim. Fr. 1985, 130-131.
27. [10j] L. Duhamel, P. Duhamel, J. E. Ancel, Tetrahedron Lett. 1994, 35, 1209-1212.
28. [10k] H. Bienayme, C. Yezeguelian, Tetrahedron 1994, 50, 3389-3396.
29. [11a] N. Nagayama, A. Kumar, K. Wuthrich, R. R. Ernst, J. Magn. Reson. 1980, 40, 321-334.
30. [11b] A. Bax, R. Freeman, G. A. Morris, J. Magn. Reson. 1981, 42, 164-168.
31. [11c] A. Bax, R. Freeman, J. Magn. Reson. 1981, 44, 542-561.
32. [11d] U. Piantini, O. W. Sorensen, R. R. Ernst, J. Am .Chem. Soc. 1982, 104, 6800-6801.
33. [11e] A. J. Shaka, R. Freeman, J. Magn. Reson. 1983, 51, 169-173.
34. [12a] L. J. Muller, J .Am. Chem. Soc. 1979, 101, 4481-4484.
35. [12b] A. Bax, R. H. Griffey, B. L. Hawkins, J. Magn. Reson. 1983, 55, 301-315.
36. [12c] M. R. Bendall, D. T. Pegg, D. M. Doddrell, J. Magn .Reson. 1983, 52, 81-117.
37. [12d] A. Bax, S. Subramanian, J. Magn. Reson. 1986, 67, 565-569.
38. [13a] A. Bax, M. F. Summers, J. Am. Chem. Soc. 1986, 108, 2093-2094.
39. [13b] M. F. Summers, L. G. Marzilli, A. Bax, J. Am. Chem. Soc. 1986, 108, 4285-4294.
40. [14a] E. J. Reist I. G. Junka, B. R. Baker, J. Org. Chem. 1960, 25, 1673-1674.
41. [14b] P. A. Wehrli, B. Schaer, Synthesis 1977, 649-650.
42. [14c] G. Eletti-Bianchi, F. Centini, L. Re, J. Org . Chem. 1976, 41, 1648-1649.
43. G. I. Zaitseva, V. M. Al' Bitskaya, Zh. Org. Chem. 1969, 5,612-617; Chem. Abstr. 1969, 71, 21638.
44. G. I. Zaitseva, V. M. Al' Bitskaya, Zh. Org. Chem. 1969, 5,612-617; Chem. Abstr. 1969, 71, 21638.
45. P. J. R. Nederlof, M. J. Moolenaar, E. R. de Waard, H. O. Huisman, Tetrahedron Lett. 1976, 3175-3178.
46. W. Oroshnik, R. A. Mallory, J. Am. Chem. Soc. 1950, 72, 4608-4613.
47. J. H. Babler, M. J. Coghlam, M. Feng, P. Fries, J .Org. Chem. 1979, 44, 1716-1717.
48. R. J. Demur, Eur. Pat. Appl. 1983, EP 82782; Chem. Abstr. 1983, 99, 175220.
49. R. J. Demur, Eur. Pat. Appl. 1983, EP 82782; Chem. Abstr. 1983, 99, 175220.
50. [20a] A. Wada C. Tude, s Hiraishi, Y. Tumala, T. Ohfusat, M. Ito, Synthesis 1995, 1107-1110.
51. [20b] H. Pommer, Angew. Chem. 1960, 22, 811-819.