Synthetic scheme for the preparation of 13C-labeled 2,7-dimethylocta-2,4,6-triene-1,8-dial, the central part of carotenoids

European Journal of Organic Chemistry

Volumn , Issue 24, 2002, Pages 4217-4221

  Van Wijk, Arjan A C ^a   Lugtenburg, Johan ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Carotenoids; Isotopic labeling; Synthesis design

Indexed keywords

2,7 DIMETHYLOCTA 2,4,6 TRIENE 1,8 DIAL C 13; ACETIC ACID; ALKENE DERIVATIVE; CARBON 13; CAROTENOID; METHYL IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ISOTOPE LABELING; SYNTHESIS;

EID: 0036910670     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200212)2002:24<4217::AID-EJOC4217>3.0.CO;2-V     Document Type: Article

References (49)

1. [1a] R. B. van Breemen, Analytical Chemistry News & Features, 1996, pp. 299A-304A.
2. [1b] Key to Carotenoids (Ed.: H. P. Pfander), Birkhäuser Verlag, Basel, 1995.
3. [1c] G. Britton, in: Carotenoids, Volume 1B: Spectroscopy (Eds.: G. Britton, S. Liaaen-Jensen, H. Pfander), Birkhäuser Verlag, Basel, 1995.
4. [2a] H. Nishino, H. Tokuda, Y. Satomi, M. Masuda, P. Bu, M. Onozuka, S. Yamaguchi, Y. Okuda, J. Takayasu, J. Tsuruta, M. Okuda, E. Ichiishi, M. Murakoshi, T. Kato, N. Misawa, T. Narisawa, N. Takasuka, M. Yano, Pure and Appl. Chem. 1999, 71 (12), 2273-2278.
5. [2b] R. M. Van Dam, Z. Huang, E. Giovanucci, et al., Am. J. Clin. Nutr. 2000, 71, 135-141.
6. [2c] U. M. Frieling, D. A. Schaumberg, T. S. Kupper, J. Muntwyler, C. H. Hennekens, Arch. Dermatol. 2000, 136, 179-184.
7. [2d] T. J. King, F. Khachik, H. Bortkiewicz, L. H. Fukushima, S. Morioka, J. S. Betram, Pure and Appl. Chem. 1997, 69(10), 2135-2140.
8. [2e] C. H. Hennekens, Pure and Appl. Chem. 1997, 69(10), 2141-2144.
9. [3a] D. M. Deming, J. W. Erdman, Pure and Appl. Chem. 1999, 71(12), 2213-2223.
10. [3b] F. Khachik, P. S. Bernstein, D. L. Garland, Invest. Ophthalmol. Vis. Sci. 1997, 38(9), 1802-1811.
11. [4a] D. A. Street, G. W Comstock, R. M. Salkeld, W. Schuep, M. J. Klag, Circulation 1994, 90, 1154-1161.
12. [4b] C. H. Hennekens, J. E. Buring, J. E. Manson, M. Stampfer, B. Rosner, N. R. Cook, C. Belanger, F. La Motte, J. M. Gaziano, P. M. Ridker, W. Willett, R. Peto, N. Engl. J. Med. 1996, 334, 1145-1149.
13. [4c] S. Liu, J. E. Manson, I. M. Lee, S. R. Cole, C. H. Hennekens, W. C. Willett, J. E. Buring, Am. Clin. Nutr. 2000, 72, 922-928.
14. [4d] W. M. R. Broekmans, Ph. D. Thesis, Wageningen University, 2002.
15. [5a] I. V. Ermakov, R. W. McClane, W. Gellermann, Optics Letters 2001, 26(4), 202-204.
16. [5b] I. V. Ermakov, M. R. Ermakova, R. W. McClane, W. Gellermann, Optics Letters 2001, 26(15), 1179-1181.
17. [5c] T. R. Hata, T. A. Scholz, I. V. Ermakov, R. W. McClane, F. Khackik, W. Gellermann, L. K. Pershing, Journ. Invest. Dermatol. 2000, 115(3), 441-447.
18. [5d] R. B. Ramanauskaite, I. G. M. J. Segers-Nolten, K. J. de Grauw, N. M. Sijtsema, L. vd Maas, J. Greve, C. Otto, C. G. Figdor, Pure and Appl. Chem. 1997, 69(10), 2131-2134.
19. [6a] R. J. Weesie, J. C. Merlin, J. Lugtenburg, G. Britton, F. J. H. M. Jansen, J. P. Cornard, Biospectroscopy 1999, 5, 19-33.
20. [6b] R. J. Weesie, J. C. Merlin, H. J. M. de Groot, G. Britton, J. Lugtenburg, E. J. H. M. Jansen, J. P. Cornard, Biospectroscopy 1999, 5, 358-370.
21. [7a] Y. Wang, X. Xu, M. van Lieshout, C. E. West, J. Lugtenburg, M. A. Verhoeven, A. F. L. Creemers, Muhilal, R. B. van Breemen, Anal. Chem. 2000, 72, 4999-5003.
22. [7b] M. van Lieshout, C. E. West, Muhilal, D. Permaeshi, Y. Wang, X. Xu, R. B. van Breemen, A. F. L. Creemers, M. A. Verhoeven, J. Lugtenburg, Am. J. Clin. Nutr. 2001, 73, 949-958.
23. A. F. L. Creemers, J. Lugtenburg, J. Am. Chem. Soc. 2002, 124, 6324-6334.
24. [9a] A. F. L. Creemers, J. Lugtenburg, J. Am. Chem. Soc. 2002, 124, 6324-6334.
25. [9b] J. Lugtenburg, A. F. L. Creemers, M. A. Verhoeven, A. A. C. van Wijk, P. J. E. Verdegem, M. C. F. Monnee, F. J. H. M. Jansen, Pure and Appl. Chem. 1999, 71 (12), 2245-2251.
26. [10a] Carotenoids, Volume 2: Synthesis (Eds.: G. Britton, S. Liaaen-Jensen, H. Pfander), Birkhäuser Verlag, Basel, 1996.
27. [10b] H. Mayer, Pure and Appl. Chem. 1994, 66(5), 931-938.
28. [10c] M. Ito, Y. Yamano, S. Sumiya, A. Wada, Pure and Appl. Chem. 1994, 66(5), 939-946.
29. [10d] H. Pommer, Angew. Chem. 1960, 72, 911-915.
30. [10e] E. Azim, P. Auzeloux, J-C. Maurizis, V. Braesco, P. Grolier, A. Veyre, J-C. Madelmont, J. Lab. Comp. Radiopharm. 1996, 38(5), 441-451.
31. [10f] P. Mildner, B. C. L. Weedon, J. Chem. Soc. 1953, 3264.
32. [10g] H. H. Inhoffen, O. Isler, G. Von der Bey, G. Raspé & P. Zeller, R. Ahrens, Ann. Chem. 1953, 580, 7-19.
33. [10h] H. H. Inhoffen, G. Von der Bey, Ann. Chem. 1953, 583, 100-109.
34. [11a] F. J. H. M. Jansen, J. Lugtenburg, in: Carotenoids, Volume 2: Synthesis (Eds.: G. Britton, S. Liaaen-Jensen, H. Pfander), Birkhäuser Verlag, Basel, 1996, pp. 233-258.
35. [11bl F. J. H. M. Jansen, M. Kwestro, D. Schmitt, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1994, 113, 552-562.
36. [11c] F. J. H. M. Jansen, J. Lugtenburg, Pure and Appl. Chem. 1994, 113, 963-972.
37. [11d] F. Khachik, G. R. Beecher, B. W. Li, G. Englert, Journal of Labelled Compounds and Radiopharmaceuticals 1995, XXXVI(12), 1157-1172.
38. W. Heinen, C. H. Rosenmöller, C. B. Wenzel, H. J. M. de Groot, J. Lugtenburg, Macromolecules 1996, 29, 1151-1157.
39. [13a] N. Ouwerkerk, J. H. van Boom, J. Lugtenburg, J. Raap, Eur. J. Org. Chem. 2000, 861-866.
40. [13b] T. M. Werkhoven, R. Van Nispen, J. Lugtenburg, Eur. J. Org. Chem. 1999, 2909-2914.
41. [13c] R. W. Lang, H-J. Hansen, Helv. Chim. Acta 1980, 63, 438-455.
42. [13d] J. H. M. Jansen, M. Kwestro, D. Schmitt, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1994, 113, 552-562.
43. [13e] F. J. H. M. Jansen, J. Lugtenburg, Pure and Appl. Chem. 1994, 113, 963-972.
44. [14a] F. J. H. M. Jansen, M. Kwestro, D. Schmitt, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1994, 113, 552-562.
45. [14b] F. J. H. M. Jansen, J. Lugtenburg, Pure and Appl. Chem. 1994, 113, 963-972.
46. 2 oxidation in the presence of the phosphorane circumvents the problem and results in double oxidation and double Wittig coupling in a one-pot reaction, which is a great improvement on the earlier work.
47. A. D. Broek, M. Muradin-Szweykowska, J. M. L. Courtin, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1983, 102, 46-51.
48. [17a] W. Heinen, C. H. Rosenmöller, C. B. Wenzel, H. J. M. de Groot, J. Lugtenburg, Macromolecules 1996, 29, 1151-1157.
49. [17b] H. H. Wasserman, C. B. Vu, Tetrahedron Lett. 1990, 31, 5205.