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Stereochemistry

  • Chapter
Carotenoids

Part of the book series: Chemische Reihe ((LMW/C,volume 23))

Abstract

The stereochemistry of carotenoids can be conveniently discussed under three main headings: (i) geometrical isomerism about the carbon-carbon double bonds, (ii) conformation about the carbon-carbon single bonds, and (iii) the absolute configuration of any chiral groups.

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References

  1. J. Herzig and F. Faltis, Ann. Chem. 431, 40 (1923).

    Google Scholar 

  2. P. Karrer, A. Helfenstein, R. Widmer and T. B. van Itallie, Helv. Chim. Acta 12, 741 (1929).

    Google Scholar 

  3. R. Kuhn and A. Winterstein, Ber. Deut. Chem. Ges. 66, 209 (1933).

    Google Scholar 

  4. A.E. Gillam and M.S. El Ridi, Nature 136, 914 (1935); Biochem. J. 30, 1735 (1936).

    Google Scholar 

  5. A.E. Gillam, M.S. El Ridi and S.K. Kon, Biochem. J. 31, 1605 (1937).

    Google Scholar 

  6. L. Zechmeister, Cis-trans Isomeric Carotenoids, Vitamins A and Arylpolyenes (Springer, Vienna 1962).

    Google Scholar 

  7. IUPAC-IUB Tentative Rules for the Nomenclature of Carotenoids, see Appendix of this book.

    Google Scholar 

  8. W. J. Rabourn, F.W. Quackenbush and J. W. Porter, Arch. Biochem. Biophys. 48, 267 (1954).

    Google Scholar 

  9. W.J. Rabourn and F.W. Quackenbush, Arch. Biochem. Biophys. 61, 111 (1956).

    Google Scholar 

  10. J.B. Davis, L.M. Jackman, P.T. Siddons and B.C.L. Weedon, J. Chem. Soc. C 1966, 2154.

    Google Scholar 

  11. O.B. Weeks, A.G. Andrewes, B.O. Brown and B.C.L. Weedon, Nature 224, 879 (1969); and unpublished results.

    Google Scholar 

  12. F.B. Jungalwala and J. W. Porter, Arch. Biochem. Biophys. 110, 291 (1965).

    Google Scholar 

  13. B.K. Koe and L. Zechmeister, Arch. Biochem. Biophys. 46, 100 (1953).

    Google Scholar 

  14. H. Claes, Z. Naturforsch. B 16, 445 (1961).

    Google Scholar 

  15. E. F. Magoon and L. Zechmeister, Arch. Biochem. Biophys. 68, 263 (1957).

    Google Scholar 

  16. A.L. Le Rosen and L. Zechmeister, J. Amer. Chem. Soc. 64, 1075 (1942).

    Google Scholar 

  17. L. Zechmeister and J.H. Pinckard, J. Amer. Chem. Soc. 69, 1930 (1947).

    Google Scholar 

  18. H. Claes, Z. Naturforsch. B 12, 401 (1957).

    Google Scholar 

  19. W. Rau and C. Zehender, Arch. Mikrobiol. 32, 423 (1959).

    Google Scholar 

  20. L. Zechmeister and W. A. Schroeder, J. Amer. Chem. Soc. 64, 1173 (1942).

    Google Scholar 

  21. N. Suzuki and K. Tsukida, Chem. Pharm. Bull. 7, 133 (1959).

    Google Scholar 

  22. B.O. Brown and B.C.L. Weedon, Chem. Commun. 1968, 382.

    Google Scholar 

  23. P. Karrer, C.H. Eugster and M. Faust, Helv. Chim. Acta 33, 300 (1950).

    Google Scholar 

  24. H.H. Strain, Arch. Biochem. Biophys. 48, 458 (1954).

    Google Scholar 

  25. J. Szabolcs and Gy. Tóth, Acta Chim. Acad. Sci. Hung. 63, 229 (1970).

    Google Scholar 

  26. H.H. Strain, W.M. Manning and G. Hardin, Biol. Bull. 86, 169 (1944).

    Google Scholar 

  27. A.L. Curl and G.F. Bailey, Food Res. 22, 323 (1957).

    Google Scholar 

  28. H. Nitsche and K. Egger, Phytochem. 8, 1577 (1969).

    Google Scholar 

  29. L. Cholnoky, K. Györgyfy, A. Rónai, J. Szabolcs, Gy. Tóth, G. Galasko, A.K. Mallams, E. S. Waight and B. C. L. Weedon, J. Chem. Soc. C 1969, 1256.

    Google Scholar 

  30. A. J. Aasen and S. Liaaen-Jensen, Acta Chem. Scand. 21, 2185 (1967).

    Google Scholar 

  31. S. Liaaen-Jensen, Pure Appl. Chem. 20, 421 (1969).

    Google Scholar 

  32. G. Wald, Angew. Chem. 80, 857 (1968).

    Google Scholar 

  33. O. Isler, Experientia 26, 225 (1970).

    Google Scholar 

  34. T. Reschke, Tetrahedron Letters 1969, 3435.

    Google Scholar 

  35. J.D. Bu’Lock, D.J. Austin, G. Snatzke and L. Hruban, Chem. Commun. 1970, 255.

    Google Scholar 

  36. P. F. Wareing and G. Ryback, Endeavour 29, 84 (1970).

    Google Scholar 

  37. S. Liaaen-Jensen, Kgl. Norske Videnskab. Selskabs Skrifter 1962, No. 8.

    Google Scholar 

  38. L. Zechmeister and R.B. Escue, J. Amer. Chem. Soc. 66, 322 (1944).

    Google Scholar 

  39. L. Zechmeister, A. L. LeRosen, W. A. Schroeder, A. Polgár and L. Pauling, J. Amer. Chem. Soc. 65, 1940 (1943).

    Google Scholar 

  40. B.C.L. Weedon, Rev. Pure Appl. Chem. (Australia) 20, 51 (1970).

    Google Scholar 

  41. L. Pauling, Fortschr. Chem. Org. Naturst. 3, 203 (1939).

    Google Scholar 

  42. N. Arpin and S. Liaaen-Jensen, Phytochem. 8, 185 (1969).

    Google Scholar 

  43. K. Schön, Biochem. J. 32, 1566 (1938).

    Google Scholar 

  44. B.C.L. Weedon, Fortschr. Chem. Org. Naturst. 27, 81 (1969).

    Google Scholar 

  45. H. H. Jaffé and M. Orchin, Theory and Applications of Ultraviolet Spectroscopy (Wiley, New York 1962).

    Google Scholar 

  46. K. Lunde and L. Zechmeister, J. Amer. Chem. Soc. 77, 1647 (1955).

    Google Scholar 

  47. M.S. Barber, J.B. Davis, L.M. Jackman and B.C.L. Weedon, J. Chem. Soc. 1960, 2870.

    Google Scholar 

  48. R.B. Bates and D.M. Gale, J. Amer. Chem. Soc. 82, 5749 (1960).

    Google Scholar 

  49. N. Nicolaides and F. Laves, J. Amer. Chem. Soc. 76, 2596 (1954).

    Google Scholar 

  50. C. v. Planta, U. Schwieter, L.H. Chopard-dit-Jean, R. Rüegg, M. Kofler and O. Isler, Helv. Chim. Acta 45, 548 (1962).

    Google Scholar 

  51. P.K. Korver, C. Kruk, P. J. van der Haak, J.L. Bass and H.O. Huisman, Tetrahedron 22, 277 (1966).

    Google Scholar 

  52. R.B. Bates, D.M. Gale and B.J. Grüner, J. Org. Chem. 28, 1086 (1963).

    Google Scholar 

  53. J. W.K. Burrell, R.F. Garwood, L.M. Jackman, E. Oskay and B.C.L. Weedon, J. Chem. Soc. C 1966, 2144.

    Google Scholar 

  54. G. Pattenden and B.C.L. Weedon, J. Chem. Soc. C 1968, 1984.

    Google Scholar 

  55. B.O. Brown, T. W. Goodwin and B.C.L. Weedon, unpublished results.

    Google Scholar 

  56. K. Tsukida, M. Yokota, H. Shimamoto and S. Cho, Vitamins (Japan) 38, 388 (1968).

    Google Scholar 

  57. K. Tsukida and M. Yokota, Vitamins (Japan) 38, 396 (1968).

    Google Scholar 

  58. U. Schwieter and S. Liaaen-Jensen, Acta Chem. Scand. 23, 1057 (1969).

    Google Scholar 

  59. P. Karrer and U. Solmssen, Helv. Chim. Acta 20, 1396 (1937).

    Google Scholar 

  60. L. Zechmeister and R.B. Escue, J. Amer. Chem. Soc. 66, 322 (1944).

    Google Scholar 

  61. P. Karrer and E. Jucker, Carotinoide (Birkhäuser, Basle 1948); English translation by E.A. Braude (Elsevier, Amsterdam 1950).

    Google Scholar 

  62. M.S. Barber, A. Hardisson, L.M. Jackman and B.C.L. Weedon, J. Chem. Soc. 1961, 1625.

    Google Scholar 

  63. L.M. Jackman and R.H. Wiley, J. Chem. Soc. 1960, 2881, 2886.

    Google Scholar 

  64. D. J. Patel, Nature 221, 825 (1969).

    Google Scholar 

  65. U. Schwieter, G. Englert, N. Rigassi and W. Vetter, Pure Appl. Chem. 20, 365 (1969).

    Google Scholar 

  66. T. W. Goodwin and R.J.H. Williams, Proc. Roy. Soc, Ser. B 163, 515 (1965).

    Google Scholar 

  67. T. W. Goodwin, Pure Appl. Chem. 20, 483 (1969).

    Google Scholar 

  68. O. Isler and P. Schudel, Advan. Org. Chem. 4, 115 (1963).

    Google Scholar 

  69. Sir Ian Heilbron and B.C.L. Weedon, Bull. Soc. Chim. France 1958, 83.

    Google Scholar 

  70. B.C.L. Weedon, Pure Appl. Chem. 20, 531 (1969).

    Google Scholar 

  71. O. Isler, H. Lindlar, M. Montavon, R. Rüegg, G. Saucy and P. Zeller, Helv. Chim. Acta 39, 2041 (1956).

    Google Scholar 

  72. O. Isler, A. Ronco, W. Guex, N.C. Hindley, W. Huber, K. Dialer and M. Kofler, Helv. Chim. Acta 32, 489 (1949).

    Google Scholar 

  73. P. Mildner and B.C.L. Weedon, J. Chem. Soc. 1953, 3294.

    Google Scholar 

  74. H. H. Inhoffen, O. Isler, G. von der Bey, G. Raspé, P. Zeller and R. Ahrens, Ann. Chem. 580, 7 (1953).

    Google Scholar 

  75. P.S. Manchand, R. Rüegg, U. Schwieter, P.T. Siddons and B.C.L. Weedon, J. Chem. Soc. 1965, 2019.

    Google Scholar 

  76. R. Kuhn, H.H. Inhoffen, H.A. Staab and W. Otting, Chem. Ber. 86, 965 (1953).

    Google Scholar 

  77. O. Isler, H. Gutmann, H. Lindlar, M. Montavon, R. Rüegg, G. Ryser and P. Zeller, Helv. Chim. Acta 39, 463 (1956).

    Google Scholar 

  78. G. Pattenden, J.E. Way and B.C.L. Weedon, J. Chem. Soc. C 1970, 235.

    Google Scholar 

  79. E. A. Braude, E. R. H. Jones, H. P. Koch, R. W. Richardson, F. Sondheimer and J. B. Toogood, J. Chem. Soc. 1949, 1890.

    Google Scholar 

  80. M. Yamaguchi, Bull. Chem. Soc. Japan 31, 51, 739 (1958); 33, 1560 (1960).

    Google Scholar 

  81. S. Liaaen-Jensen, E. Hegge and L.M. Jackman, Acta Chem. Scand. 18, 1703 (1964).

    Google Scholar 

  82. R. Bonnett, A.A. Spark and B.C.L. Weedon, Acta Chem. Scand. 18, 1739 (1964).

    Google Scholar 

  83. R. D. G. Cooper, J. B. Davis and B. C. L. Weedon, J. Chem. Soc. 1963, 5637.

    Google Scholar 

  84. S. Hertzberg, S. Liaaen-Jensen, C.R. Enzell and G.W. Francis, Acta Chem. Scand. 23, 3290 (1969).

    Google Scholar 

  85. E.L. Eichhorn and C.H. MacGillavry, Acta Crystallogr. 12, 872 (1959).

    Google Scholar 

  86. B. Koch and C.H. MacGillavry, Acta Crystallogr. 16, A 48 (1963).

    Google Scholar 

  87. C.H. Stam and C.H. MacGillavry, Acta Crystallogr. 16, 62 (1963).

    Google Scholar 

  88. C. Sterling, Acta Crystallogr. 17, 1224 (1964).

    Google Scholar 

  89. J.C. J. Bart and C.H. MacGillavry, Acta Crystallogr., Sect. B 24, 1587 (1968).

    Google Scholar 

  90. W.G. Sly, Acta Crystallogr. 17, 511 (1964).

    Google Scholar 

  91. J.C. J. Bart and C.H. MacGillavry, Acta Crystallogr., Sect. B 24, 1569 (1968).

    Google Scholar 

  92. C. A. Coulson, J. Chem. Phys. 7, 1069 (1939).

    Google Scholar 

  93. H.H. Inhoffen, F. Bohlmann, K. Bartram, G. Rummert and H. Pommer, Ann. Chem. 570, 54 (1950).

    Google Scholar 

  94. B. Pullman, J. Langlet and H. Berthod, J. Theor. Biol. 23, 492 (1969).

    Google Scholar 

  95. L. Zechmeister, L. Cholnoky and A. Polgár, Ber. Deut. Chem. Ges. 72, 1678 (1939).

    Google Scholar 

  96. R. Kuhn and C. Grundmann, Ber. Deut. Chem. Ges. 67, 596 (1934).

    Google Scholar 

  97. L. Zechmeister and L. Cholnoky, Ann. Chem. 543, 248 (1940).

    Google Scholar 

  98. I.M. Heilbron and R.F. Phipers, Biochem. J. 29, 1369 (1935).

    Google Scholar 

  99. P. Karrer, A. Helfenstein, H. Wehrli, B. Pieper and R. Morf, Helv. Chim. Acta 14, 614 (1931).

    Google Scholar 

  100. L. Zechmeister and P. Tuzson, Ber. Deut. Chem. Ges. 62, 2226 (1929).

    Google Scholar 

  101. R. Kuhn, A. Winterstein and E. Lederer, Hoppe-Seyler’s Z. Physiol. Chem. 197, 141 (1931).

    Google Scholar 

  102. P. Karrer and O. Walker, Helv. Chim. Acta 16, 641 (1933).

    Google Scholar 

  103. R. Kuhn and E. Lederer, Ber. Deut. Chem. Ges. 64, 1349 (1931).

    Google Scholar 

  104. P. Karrer, E. Jucker and J. Rutschmann, Helv. Chim. Acta 28, 1156 (1945).

    Google Scholar 

  105. R. Kuhn and A. Deutsch, Ber. Deut. Chem. Ges. 66, 883 (1933).

    Google Scholar 

  106. H.H. Strain, J. Biol. Chem. 123, 425 (1938).

    Google Scholar 

  107. A.L. Le Rosen and L. Zechmeister, Arch. Biochem. 1, 17 (1943).

    Google Scholar 

  108. R. Kuhn, A. Winterstein and W. Kaufmann, Ber. Deut. Chem. Ges. 63, 1489 (1930).

    Google Scholar 

  109. O. Isler, H. Lindlar, M. Montavon, R. Rüegg, G. Saucy and P. Zeller, Helv. Chim. Acta 39, 2041 (1956).

    Google Scholar 

  110. O. Isler, H. Lindlar, M. Montavon, R. Rüegg, G. Saucy and P. Zeller, Helv. Chim. Acta 40, 456 (1957).

    Google Scholar 

  111. R. Bonnett, A.K. Mallams, A.A. Spark, J.L. Tee, B.C.L. Weedon and A. McCormick, J. Chem. Soc. C 1969, 429.

    Google Scholar 

  112. P. Karrer, R. Morf, E. v. Krauss and A. Zubrys, Helv. Chim. Acta 15, 490 (1932).

    Google Scholar 

  113. N.J. Antia, Can. J. Chem. 43, 302 (1965).

    Google Scholar 

  114. L. Bartlett, W. Klyne, W. P. Mose, P. M. Scopes, G. Galasko, A. K. Mallams, B.C.L. Weedon, J. Szabolcs and Gy.Tóth, J. Chem. Soc. C 1969, 2527.

    Google Scholar 

  115. D. Goodfellow, W. Klyne, G.P. Moss, P.M. Scopes and B.C.L. Weedon, unpublished results.

    Google Scholar 

  116. M. Buchwald and W.P. Jencks, Biochemistry 7, 834, 844 (1968).

    Google Scholar 

  117. S. Liaaen-Jensen, private communication.

    Google Scholar 

  118. M.S. Barber, L.M. Jackman, C.K. Warren and B.C.L. Weedon, Proc. Chem. Soc. 1960, 19; J. Chem. Soc. 1961, 4019.

    Google Scholar 

  119. R. Entschel and P. Karrer, Helv. Chim. Acta 43, 89 (1960).

    Google Scholar 

  120. H. Faigle and P. Karrer, Helv. Chim. Acta 44, 1257 (1961).

    Google Scholar 

  121. H. Faigle and P. Karrer, Helv. Chim. Acta 44, 1904 (1961).

    Google Scholar 

  122. L. Cholnoky and J. Szabolcs, Experientia 16, 483 (1960).

    Google Scholar 

  123. K. Freudenberg and W. Lwowski, Ann. Chem. 587, 213 (1954); 594, 76 (1955).

    Google Scholar 

  124. R.D.G. Cooper, L.M. Jackman and B.C.L. Weedon, Proc. Chem. Soc. 1962, 215.

    Google Scholar 

  125. J. W. Faigle, H. Müller, W. von Philipsborn and P. Karrer, Helv. Chim. Acta 47, 741 (1964).

    Google Scholar 

  126. R. Bowden and B.C.L. Weedon, unpublished results.

    Google Scholar 

  127. B.C.L. Weedon, Chem. in Britain 3, 424 (1967).

    Google Scholar 

  128. J. Bredt, Ann. Chem. 395, 26 (1913).

    Google Scholar 

  129. A. Marquet, M. Dvolaitzky and D. Arigoni, Bull. Soc. Chim. France 1966, 2956. Carotenoids 21

    Google Scholar 

  130. F.H. Allen and D. Rogers, Chem. Commun. 1966, 837.

    Google Scholar 

  131. A. Jensen, Acta Chem. Scand. 15, 1605 (1961).

    Google Scholar 

  132. L. Cholnoky, J. Szabolcs and Gy. Tóth, Ann. Chem. 708, 218 (1967).

    Google Scholar 

  133. J.S. Narozanski, S.W. Russell and B.C.L. Weedon, unpublished results.

    Google Scholar 

  134. P. Nayler and M.C. Whiting, J. Chem. Soc. 1954, 4006.

    Google Scholar 

  135. T. Miki and Y. Hara, Pharm. Bull. 4, 89 (1956).

    Google Scholar 

  136. S.W. Russell and B.C.L. Weedon, Chem. Commun. 1969, 85.

    Google Scholar 

  137. S.W. Russell and B.C.L. Weedon, unpublished results.

    Google Scholar 

  138. T.E. DeVille, M. B. Hursthouse, S.W. Russell and B. C. L. Weedon, Chem. Commun. 1969, 754.

    Google Scholar 

  139. T.E. DeVille, M. B. Hursthouse, S.W. Russell and B. C. L. Weedon, Chem. Commun. 1969, 1311.

    Google Scholar 

  140. J.M. Bijvoet, Endeavour 14, 71 (1955).

    Google Scholar 

  141. G. Galasko, J. Hora, T.P. Toube, B. C. L. Weedon, D. André, M. Barbier, E. Lederer and V.R. Villanueva, J. Chem. Soc. C 1969, 1264.

    Google Scholar 

  142. J. Hora, T.P. Toube and B.C.L. Weedon, J. Chem. Soc. C 1970, 241.

    Google Scholar 

  143. H.F. Taylor and R.S. Burden, Phytochem. 9, 2217 (1970).

    Google Scholar 

  144. P. Karrer, Fortschr. Chem. Org. Naturst. 5, 1 (1948).

    Google Scholar 

  145. P. Karrer and E. Jucker, Helv. Chim. Acta 28, 300 (1945).

    Google Scholar 

  146. J. Meinwald, K. Erickson, M. Hartshorn, Y.C. Meinwald and T. Eisner, Tetrahedron Letters 1968, 2959.

    Google Scholar 

  147. J. Meinwald and L. Hendry, Tetrahedron Letters 1969, 1657.

    Google Scholar 

  148. S. Isoe, S.B. Hyeon, H. Ichikawa, S. Katsumura and T. Sakan, Tetrahedron Letters 1968, 5561.

    Google Scholar 

  149. M. Mousseron-Canet, J.-P. Dalle and J.-C. Mani, Tetrahedron Letters 1968, 6037.

    Google Scholar 

  150. C.S. Foote and M. Brenner, Tetrahedron Letters 1968, 6041.

    Google Scholar 

  151. D.E. Loeber, S.W. Russell, T.RToube and B.C.L. Weedon, J. Chem. Soc. C 1971, 404.

    Google Scholar 

  152. T.E. DeVille, J. Hora, M.B. Hursthouse, T.RToube and B.C.L. Weedon, Chem. Commun. 1970, 1231.

    Google Scholar 

  153. W. Fenical, D.R. Kearns and P. Radlick, J. Amer. Chem. Soc. 91, 3396 (1969).

    Google Scholar 

  154. D.R. Kearns, J. Amer. Chem. Soc. 91, 6554 (1969).

    Google Scholar 

  155. K. Tsukida, S. Cho and M. Yokota, Chem. Pharm. Bull. 17, 1755 (1969)

    Google Scholar 

  156. L. Hendry, private communication.

    Google Scholar 

  157. J.W Cornforth, W. Draber, B.V. Milborrow and G. Ryback, Chem. Commun. 1967, 114.

    Google Scholar 

  158. J.W. Cornforth, B.V. Milborrow and G. Ryback, Nature 206, 715 (1965).

    Google Scholar 

  159. J. A. Mills, J. Chem. Soc. 1952, 4976.

    Google Scholar 

  160. P.F. Wareing and G. Ryback, Endeavour 29, 84 (1970).

    Google Scholar 

  161. H.F. Taylor and T.A. Smith, Nature 215, 1513 (1967).

    Google Scholar 

  162. H.F. Taylor, Soc. Chem. Ind. London Monograph 1968, No. 31, 22.

    Google Scholar 

  163. T. Wada, Chem. Pharm. Bull. 13, 43 (1965).

    Google Scholar 

  164. G. Snatzke, H. Schwang and P. Welzel, Some New Methods in Structural Chemistry (United Trade Press, London 1967).

    Google Scholar 

  165. A.J. Davies and B.C.L. Weedon, unpublished results.

    Google Scholar 

  166. H. Sobotka, E. Bloch, H. Cahnmann, E. Feldbau and E. Rosen, J. Amer. Chem. Soc. 65, 2061 (1943).

    Google Scholar 

  167. C. Tscharner, C. H. Eugster and P. Karrer, Helv. Chim. Acta 40, 1676 (1957); 41, 32 (1958).

    Google Scholar 

  168. C.H. Eugster, R. Buchecker, C. Tscharner, G. Uhde and G. Ohloff, Helv. Chim. Acta 52, 1729 (1969).

    Google Scholar 

  169. R. Buchecker, H. Yokoyama and C. H. Eugster, Helv. Chim. Acta 53, 1210 (1970).

    Google Scholar 

  170. Y.R. Naves and G.R. Parry, Helv. Chim. Acta 30, 419 (1947).

    Google Scholar 

  171. Y.R. Naves, Helv. Chim. Acta 32, 1064 (1949).

    Google Scholar 

  172. D. La Face, Helv. Chim. Acta 33, 249 (1950).

    Google Scholar 

  173. Y. R. Naves, Perfum. Essent. Oil Rec. 55, 658 (1964).

    Google Scholar 

  174. M. Winter and E. Sundt, Helv. Chim. Acta 45, 2195 (1962).

    Google Scholar 

  175. M. Soucek and P. Vlad, Collect. Czech. Chem. Commun. 28, 1211 (1963).

    Google Scholar 

  176. B.C.L. Weedon, in Chemistry and Biochemistry of Plant Pigments, ed. by T.W. Goodwin (Academic Press, London 1965), p. 86.

    Google Scholar 

  177. H. Müller and P. Karrer, Helv. Chim. Acta 48, 291 (1965).

    Google Scholar 

  178. T.J. Walton, G. Britton and T.W. Goodwin, Biochem. J. 112, 383 (1969).

    Google Scholar 

  179. D. Goodfellow, G.P. Moss and B.C.L. Weedon, Chem. Commun. 1970, 1578.

    Google Scholar 

  180. E. Nicoară, G. Illyes, M. Şuteu and C. Bodea, Rev. Roumaine Chim. 12, 547 (1967).

    Google Scholar 

  181. D.J. Austin, J.D. Bu’Lock and D. Drake, Experientia 26, 348 (1970).

    Google Scholar 

  182. W. V. E. Doering and R. W. Young, J. Amer. Chem. Soc. 74, 2997 (1952).

    Google Scholar 

  183. G. Snatzke and K. Schaffner, Helv. Chim. Acta 51, 986 (1968).

    Google Scholar 

  184. R.S. Cahn and C.K. Ingold, J. Chem. Soc. 1951, 612.

    Google Scholar 

  185. R.S. Cahn, C.K. Ingold and V. Prelog, Experientia 12, 81 (1956).

    Google Scholar 

  186. R.S. Cahn, Sir Christopher Ingold and V. Prelog, Angew. Chem., Int. Ed. Engl. 5, 385 (1966).

    Google Scholar 

  187. R.S. Cahn, J. Chem. Educ. 41, 116 (1964).

    Google Scholar 

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Weedon, B.C.L. (1971). Stereochemistry. In: Isler, O., Gutmann, H., Solms, U. (eds) Carotenoids. Chemische Reihe, vol 23. Birkhäuser, Basel. https://doi.org/10.1007/978-3-0348-5831-1_5

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  • DOI: https://doi.org/10.1007/978-3-0348-5831-1_5

  • Publisher Name: Birkhäuser, Basel

  • Print ISBN: 978-3-0348-5832-8

  • Online ISBN: 978-3-0348-5831-1

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