Abstract
In some important examples of naturally occurring carotenoids, the polyene chain is modified by the presence of one or two acetylenic or allenic groups. These and other interesting features are illustrated by peridinin (558) and pyrrhoxanthin (556) which contain allenic and acetylenic groups, respectively, as well as unusual modifications such as a C37-skeleton with an abnormal arrangement of side-chain methyl groups, and the presence of a butenolide structure. The synthesis of such carotenoids, particularly in the natural optically active form, provides a major challenge and the syntheses that have been developed are described in this Chapter.
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References
O. Puntervold and S. Liaaen-Jensen, Acta Chem. Scand., B28, 1096 (1974).
J. E. Johansen and S. Liaaen-Jensen, Tetrahedron, 381 (1977).
P. A. Butikofer and C. H. Eugster, Helv. Chim. Acta, 4, 1148 (1983).
A. J. Davies, A. Khare, A. K. Mallams, R. A. Massy-Westropp, G. P. Moss and B. C. L. Weedon, J. Chem. Soc., Perkin Trans. 1, 2147 (1984).
J. A. Haugan and S. Liaaen-Jensen, Acta Chem. Scand., 48, 899 (1994).
J. A. Haugan and S. Liaaen-Jensen, Tetrahedron Asymmetry, 5, 1781 (1994).
K. Bernhard, Abstr. 6th Int. Symp. on Carotenoids, Liverpool (1981).
J. Meinwald and L. Hendry, Tetrahedron Lett., 1657 (1969).
S. Isoe, S. Katsumura, S. Be Hyeon and T. Sakan, Tetrahedron Lett., 1089 (1971).
J. R. Hlubucek, J. Hora, S. W. Russell, T. P. Toube and B. C. L. Weedon, J. Chem. Soc., Perkin Trans. 1, 848 (1974).
K. Mori, Tetrahedron, 30, 1065 (1974).
T. Bjørnland, G. Englert, K. Bernhard and S. Liaaen-Jensen, Tetrahedron Lett., 30, 2577 (1989).
A. Baumeler, W. Brade, A. Haag and C. H. Eugster, Helv. Chim. Acta, 73, 700 (1990).
A. Baumeler and C. H. Eugster, Helv. Chim. Acta, 74, 469 (1991).
E. Widmer, Pure Appl. Chem., 57, 741 (1985).
M. Ito, Y. Hirata, K. Tsukida, N. Tanaka, K. Hamada, R. Hino and T. Fujiwara, Chem. Pharm. Bull., 36, 3328 (1988).
Y. Yamano and M. Ito, J. Chem. Soc., Perkin Trans. 1, 1599 (1993).
M. Ito, Y. Hirata, Y. Shibata and K. Tsukida, J. Chem. Soc., Perkin Trans. 1, 197 (1990).
M. Ito, Y. Katsuta, Y. Yamano and K. Tsukida, J. Chem. Soc., Perkin Trans. 1, 987 (1993).
M. Ito, Pure Appl. Chem., 63, 13 (1991).
M. Ito, Y. Yamano and Y. Shibata, Meth. Enzymol., 213, 13 (1992).
A. K. Chopra, G. P. Moss and B. C. L. Weedon, J. Chem. Soc., Perkin Trans. 1, 1371 (1988).
A. K. Chopra, A. Khare, G. P. Moss and B. C. L. Weedon, J. Chem. Soc., Perkin Trans. 1, 1383 (1988).
F. R. Ahmed and T. P. Toube, J. Chem. Soc., Perkin Trans. 1, 1577 (1984).
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© 1996 Birkhäuser Verlag Basel
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Ito, M. (1996). Synthesis of Acetylenic, Allenic and In-chain Substituted Carotenoids. In: Britton, G., Liaaen-Jensen, S., Pfander, H. (eds) Carotenoids. Carotenoids, vol 2. Birkhäuser Basel. https://doi.org/10.1007/978-3-0348-9323-7_11
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DOI: https://doi.org/10.1007/978-3-0348-9323-7_11
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