New Synthesis of Natural Carotene Isorenieratene (φ,φ-Carotene) and its 3,3′-Dimethoxy Analogue

Helvetica Chimica Acta

Volumn 86, Issue 10, 2003, Pages 3314-3319

  Valla, Alain R ^a   Cartier, Dominique L ^b   Valla, Benoist G ^b   Le Guillou, Régis Y ^b   Andriamialisoa, Zo R ^b   Labia, Roger ^b   Breithaupt, Dietmar E ^c   Savy, Stéphanie M ^d   Binet, Adrien ^d   Dufossé, Laurent H ^d  

^a VA R/D Pepiniere d'Entreprises 140 ^*  (France)

^b Chim et Biol Substances Naturelles   (France)

^c UNIVERSITY OF HOHENHEIM   (Germany)

^d UNIVERSITÉ DE BRETAGNE OCCIDENTALE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; BACTERIA; PIGMENTS;

ANALOGUES;

SYNTHESIS (CHEMICAL);

CAROTENE; CAROTENOID; ISORENIERATENE; UNCLASSIFIED DRUG; XANTHOPHYLL;

ARTICLE; BREVIBACTERIUM LINENS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PHOTOTROPHIC BACTERIUM; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0242696169     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200390273     Document Type: Article

References (33)

1. S. Liaaen-Jensen, Acta Chem. Scand. 1965, 19, 1025.
2. W. Kohl, A. Achenbach, H. Reichenbach, Phytochem. 1983, 22, 207; F. Guyomarc'h, A. Binet, L. Dufossé, J. Ind. Microbiol. Biotech. 2000, 24, 64.
3. W. Kohl, A. Achenbach, H. Reichenbach, Phytochem. 1983, 22, 207; F. Guyomarc'h, A. Binet, L. Dufossé, J. Ind. Microbiol. Biotech. 2000, 24, 64.
4. M. Viveiros, P. Krubasik, G. Sandmann, M. Houssaini-Iraqui, FEMS Microbiol. Lett. 2000, 187, 95; M. Houssaini-Iraqui, H. L. David, S. Clavel-Sérès, F. Hilali, N. Rastogi, Curr. Microbiol. 1993, 27, 317; M. Houssaini-Iraqui, S. Clavel-Sérès, N. Rastogi, H. L. David, Curr. Microbiol. 1993, 27, 317.
5. M. Viveiros, P. Krubasik, G. Sandmann, M. Houssaini-Iraqui, FEMS Microbiol. Lett. 2000, 187, 95; M. Houssaini-Iraqui, H. L. David, S. Clavel-Sérès, F. Hilali, N. Rastogi, Curr. Microbiol. 1993, 27, 317; M. Houssaini-Iraqui, S. Clavel-Sérès, N. Rastogi, H. L. David, Curr. Microbiol. 1993, 27, 317.
6. M. Viveiros, P. Krubasik, G. Sandmann, M. Houssaini-Iraqui, FEMS Microbiol. Lett. 2000, 187, 95; M. Houssaini-Iraqui, H. L. David, S. Clavel-Sérès, F. Hilali, N. Rastogi, Curr. Microbiol. 1993, 27, 317; M. Houssaini-Iraqui, S. Clavel-Sérès, N. Rastogi, H. L. David, Curr. Microbiol. 1993, 27, 317.
7. F. Arcamone, B. Camerino, E. Cotta, G. Franceschi, A. Grein, S. Penco, C. Spalla, Experientia 1969, 25, 241.
8. R. Buchecker, C. H. Eugster, C. Litchfield, Helv. Chim. Acta 1977, 69, 2780.
9. 'Carotenoids', Ed. O. Isler, Birkhäuser Verlag, Basel, Stuttgart, 1971; M. B. Sporn, A. B. Roberts, D. S. Goodman, 'The Retinoids'; Vol. 1, Academic Press, Orlando, 1984; M. B. Sporn, A. B. Roberts, D. S. Goodman, 'The Retinoids: Biology, Chemistry, and Medicine', Raven Press, New York, 1994.
10. 'Carotenoids', Ed. O. Isler, Birkhäuser Verlag, Basel, Stuttgart, 1971; M. B. Sporn, A. B. Roberts, D. S. Goodman, 'The Retinoids'; Vol. 1, Academic Press, Orlando, 1984; M. B. Sporn, A. B. Roberts, D. S. Goodman, 'The Retinoids: Biology, Chemistry, and Medicine', Raven Press, New York, 1994.
11. 'Carotenoids', Ed. O. Isler, Birkhäuser Verlag, Basel, Stuttgart, 1971; M. B. Sporn, A. B. Roberts, D. S. Goodman, 'The Retinoids'; Vol. 1, Academic Press, Orlando, 1984; M. B. Sporn, A. B. Roberts, D. S. Goodman, 'The Retinoids: Biology, Chemistry, and Medicine', Raven Press, New York, 1994.
12. G. Wittig, G. Geissler, Liebig's Ann. Chem. 1953, 580, 44.
13. M. Julia, D. Arnould, Bull. Soc. Chim. Fr. 1973, 743.
14. J. E. McMurry, J. Am. Chem. Soc. 1974, 96, 4708; J. E. McMurry, Chem. Rev. 1989, 89, 1513.
15. J. E. McMurry, J. Am. Chem. Soc. 1974, 96, 4708; J. E. McMurry, Chem. Rev. 1989, 89, 1513.
16. S. Akiyama, S. Nakatsuji, S. Eda, M. Kataoka, M. Nakagawa, Tetrahedron Lett. 1979, 30, 2813.
17. M. Yamaguchi, Bull. Chem. Soc. Jpn. 1959, 32, 1171.
18. N. Okukado, Bull. Chem. Soc. Jpn. 1974, 47, 2345.
19. R. D. G. Cooper, J. B. Davis, B. C. L. Weedon, J. Chem. Soc. 1963, 5637.
20. Z. Andriamialisoa, A. Valla, D. Cartier, R. Labia, Helv. Chim. Acta 2002, 85, 2926.
21. L. Duhamel, P. Tombret, J. Org. Chem. 1981, 46, 3741.
22. L. Duhamel, P. Duhamel, J. E. Ancel, Tetrahedron Lett. 1994, 35, 1209.
23. S. M. Makin, I. E. Mikerin, E. K. Dobrestova, O. A. Shavrygina, Zhu. Org. Khim. 1993, 29, 682.
24. B. A. Pawson, K. Chan, R. DeNoble, R. Han, V. Piermattie, A. C. Specian, S. Srisethnil, W. T. Trown, O. Bohoslawec, L. J. Machlin, E. Gabriel, J. Med. Chem. 1979, 22, 1059, and refs. cited therein.
25. A. Valla, Z. Andriamialisoa, V. Prat, A. Laurent, M. Giraud, R. Labia, P. Potier, Tetrahedron 2000, 56, 7211.
26. D. E. Breithaupt, U. Wirt, A. Bamedi, J. Agric. Food Chem. 2002, 50, 66.
27. T. Matsuno, T. Maoka, K. Katagiri, T. Komori, Nippon Suisan Gakkaishi 1984, 50, 1071.
28. G. W. Francis, Acta Chem. Scand. 1972, 26, 1443.
29. H. Kjoesen, S. Liaaen-Jensen, Acta Chem. Scand. 1971, 25, 85.
30. J. Paust, P. S. Manchand, in 'Carotenoids', Vol. 2, Ed. G. Britton, S. Liaaen-Jensen, H. Pfander, Birkhäuser Verlag, Basel, 1996, p. 329.
31. G. Englert, in 'Carotenoids, Vol. 1B: Spectroscopy', Ed. G. Britton, S. Liaaen-Jensen, H. Pfander, Birkhäuser Verlag, Basel, 1995, p. 179, ex: 103; N. Okukado, Bull. Soc. Chim. Jpn 1974, 47, 2345; S. Akiyama, S. Nakatsuji, S. Eda, M. Kataoka, M. Nakagawa, Tetrahedron Lett. 1979, 30, 2813.
32. G. Englert, in 'Carotenoids, Vol. 1B: Spectroscopy', Ed. G. Britton, S. Liaaen-Jensen, H. Pfander, Birkhäuser Verlag, Basel, 1995, p. 179, ex: 103; N. Okukado, Bull. Soc. Chim. Jpn 1974, 47, 2345; S. Akiyama, S. Nakatsuji, S. Eda, M. Kataoka, M. Nakagawa, Tetrahedron Lett. 1979, 30, 2813.
33. G. Englert, in 'Carotenoids, Vol. 1B: Spectroscopy', Ed. G. Britton, S. Liaaen-Jensen, H. Pfander, Birkhäuser Verlag, Basel, 1995, p. 179, ex: 103; N. Okukado, Bull. Soc. Chim. Jpn 1974, 47, 2345; S. Akiyama, S. Nakatsuji, S. Eda, M. Kataoka, M. Nakagawa, Tetrahedron Lett. 1979, 30, 2813.