Revisited after 50 years: The 'stereochemical interpretation of the biogenetic isoprene rule for the triterpenes'

Helvetica Chimica Acta

Volumn 88, Issue 12, 2005, Pages 3011-3050

  Eschenmoser, Albert ^a,b   Arigoni, Duilio ^a  

^a ETH ZURICH   (Switzerland)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMYRIN; EUPHOL; FERNENOL; FRIEDELIN; GERMANICOL; ISOARBORINOL; ISOPRENE; LANOSTEROL; LUPEOL; SQUALENE; TARAXASTEROL; TIRUCALLOL; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

BIOGENESIS; CHEMICAL STRUCTURE; CHIMERA; CYCLIZATION; DERIVATIZATION; PRIORITY JOURNAL; REVIEW; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 30144439471     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200590245     Document Type: Review

References (153)

1. V. Prelog, O. Jeger, Biogr. Mem. Fellows R. Soc. (London) 1980, 26, 411.
2. C. Ganter, Chimia 1977, 31, 286;
3. K. Schaffner, Chimia 1985, 39, 336;
4. K. Schaffner, Chimia 1992, 46, 450;
5. J. J. Bonet Sugranes, Afinidad 2002, 59, 498.
6. A. Eschenmoser, L. Ruzicka, O. Jeger, D. Arigoni, Helv. Chim. Acta 1955, 38, 1890.
7. J. W. Cornforth, Pure Appl. Chem. 1961, 2, 607.
8. G. Stork, A. W. Burgstahler, J. Am. Chem. Soc. 1955, 77, 5068.
9. R. A. Yoder, J. N. Johnston, Chem. Rev., in press.
10. K. U. Wendt, K. Poralla, G. E. Schulz, Science 1997, 277, 1811.
11. a) D. J. Reinert, G. Balliano, G. E. Schulz, Chem. Biol. 2004, 11, 121.
12. b) R. Thoma, T. Schulz-Gasch, B. D'Arcy, J. Benz, J. Aebi, H. Dehmlow, M. Hennig, M. Stihle, A. Ruf, Nature 2004, 432, 118.
13. a) J. H. Richards, J. B. Hendrickson, 'The Biosynthesis of Steroids, Terpenes and Acetogenins', W. A. Benjamin Inc., New York, 1964;
14. b) R. B. Clayton, Quart. Rev., Chem. Soc. 1965, 19, 168;
15. c) D. E. Cane, Acc. Chem. Res. 1985, 18, 220;
16. d) I. Abe, M. Rohmer, G. D. Prestwich, Chem. Rev. 1993, 93, 2189;
17. e) K. U. Wendt, G. E. Schulz, E. J. Corey, D. R. Liu, Angew. Chem. 2000, 112, 2930;
18. Angew. Chem., Int. Ed. 2000, 39, 2812;
19. f) R. Xu, G. C. Fazio, S. P. T. Matsuda, Phytochemistry 2004, 65, 261;
20. g) K. U. Wendt, Angew. Chem., Int. Ed. 2005, 44, 3966;
21. h) W. Eisenreich, A. Bacher, D. Arigoni, F. Rohdich, Cell. Mol. Life Sci. 2004, 61, 1401.
22. O. Wallach, Liebigs Ann. Chem. 1887, 239, 1;
23. O. Wallach, 'Terpene und Campher', Verlag Veit & Co., Leipzig, 1909.
24. L. Ruzicka, Angew. Chem. 1938, 51, 5;
25. Les Prix Nobel en 1945, Nobel Foundation, Stockholm (1947).
26. a) L. Ruzicka, Experientia 1953, 9, 357;
27. b) L. Ruzicka 'together with A. Eschenmoser and H. Heusser', Experientia 1953, 9, 362
28. ('Biogenesis of Steroids and Terpenic Compounds'; last chapter in [12a]).
29. F. Tiemann, P. Krüger, Ber. Dtsch. Chem. Ges. 1893, 26, 2675.
30. a) F. Zobrist, H. Schinz, Helv. Chim. Acta 1949, 32, 1192;
31. J.-P. Bourquin, H. L. Simon, G. Schäppi, U. Steiner, H. Schinz, Helv. Chim. Acta 1949, 32, 1564;
32. b) A. Caliezi, H. Schinz, Helv. Chim. Acta 1949, 32, 2556;
33. A. Caliezi, H. Schinz, Helv. Chim. Acta 1950, 33, 1129;
34. A. Caliezi, H. Schinz, Helv. Chim. Acta 1952, 35, 1637;
35. A. Lauchenauer, H. Schinz, Helv. Chim. Acta 1951, 34, 1514;
36. R. Helg, H. Schinz, Helv. Chim. Acta 1952, 35, 2406;
37. H. Kappeler, A. Eschenmoser, H. Schinz, Helv. Chim. Acta 1953, 36, 1877;
38. H. Kappeler, D. Stauffacher, A. Eschenmoser, H. Schinz, Helv. Chim. Acta 1954, 37, 957;
39. R. Helg, F. Zobrist, A. Lauchenauer, K. Brack, A. Caliezi, D. Stauffacher, E. Zweifel, H. Schinz, Helv. Chim. Acta 1956, 39, 1269.
40. A. Eschenmoser, Diplomarbeit, ETH Zürich, 1948;
41. A. Eschenmoser, H. Schinz, Helv. Chim. Acta 1950, 33, 171.
42. A. Eschenmoser, 'Zur säurekatalysierten Zyklisierung bei Mono- und Sesquiterpenverbindungen', Ph.D. Thesis No. 2018, ETH-Zurich, February 1951 (printed 1952, Juris-Verlag, Zurich). Full text available at: http://e-collection.ethbib.ethz.ch/ecol-pool/diss/fulltext/eth2018.pdf
43. L. Ruzicka, M. Stoll, Helv. Chim. Acta 1922, 5, 923.
44. L. Ruzicka, E. Capato, Helv. Chim. Acta 1925, 8, 259.
45. D. E. Cane, in 'Comprehensive Natural Products Chemistry, Vol. 2, Isoprenoids Including Carotenoids and Steroids', Ed. D. E. Cane, Elsevier, Amsterdam, 1999, Chapt. 2.06, p. 155-200; a) paragraph 2.06.2; b) paragraph 2.06.1.
46. A. Eschenmoser, Chimia 1990, 44, 1
47. (English translation by E. Loewenthal of the article of A. E., 'Leopold Ruzicka - From the Isoprene Rule to the Question of Life's Origin', original version in German, published in the Ruzicka Centenary Issue of Rad, the Journal of the Yugoslavian Academy of Sciences and Arts, Zagreb, 1989, 7, 21.)
48. K. Bloch, 'The Biological Synthesis of Cholesterol', Les Prix Nobel en 1964, P. A. Norstedt & Söner, Stockholm, 1965.
49. a) W. Voser, M. V. Mijovic, H. Heusser, O. Jeger, L. Ruzicka, Helv. Chim. Acta 1952, 35, 2414;
50. b) R. G. Curtis, J. Fridrichsons, A. McL. Mathieson, Nature 1952, 170, 321;
51. J. Fridrichsons, A. McL. Mathieson, J. Chem. Soc. 1953, 2159.
52. C. S. Barnes, D. H. R. Barton, J. S. Fawcett, B. R. Thomas, J. Chem. Soc. 1952, 2339.
53. R. B. Woodward, K. Bloch, J. Am. Chem. Soc. 1953, 75, 2023.
54. R. Robinson, Chem. Ind. (London) 1934, 53, 1062.
55. H. J. Channon, G. F. Marrian, Biochem. J. 1926, 20, 409.
56. M. Vanghelovici, Chem. Ind. (London) 1934, 53, 998.
57. W. M. D. Bryant, Chem. Ind. (London) 1935, 54, 907, 1082.
58. L. Ruzicka, J. R. Hosking, Helv. Chim. Acta 1931, 14, 203 (see p. 210).
59. I. M. Heilbron, E. D. Kamm, W. M. Owens, J. Chem. Soc. 1926, 1630.
60. A. Mondon, Angew. Chem. 1953, 65, 333.
61. T. T. Tchen, K. Bloch, J. Am. Chem. Soc. 1955, 77, 6085.
62. R. B. Clayton, K. Bloch, J. Biol. Chem. 1956, 218, 305, 319.
63. T. L. Dawson, G. R. Ramage, B. Wilson, Chem. Ind. (London) 1951, 464.
64. D. H. R. Barton, T. Bruun, A. S. Lindsey, Chem. Ind. (London) 1951, 910.
65. A. Eschenmoser, A. Fürst, Experientia 1951, 7, 290.
66. A. Eschenmoser, H. H. Günthard, Helv. Chim. Acta 1951, 34, 2338.
67. D. H. R. Barton, T. Bruun, A. S. Lindsey, J. Chem. Soc. 1952, 2210.
68. P. A. Plattner, A. Fürst, A. Eschenmoser, W. Keller, H. Kläui, S. Meyer, M. Rosner, Helv. Chim. Acta 1953, 36, 1845.
69. G. Stork, R. Breslow, J. Am. Chem. Soc. 1953, 75, 3291.
70. 'Dictionary of Natural Products', Chapman & Hall, London, 1994; database version (2004): www.chemnetbase.com/scripts/dnpweb.exe
71. D. Arigoni, R. Viterbo, M. Dünnenberger, O. Jeger, L. Ruzicka, Helv. Chim. Acta 1954, 37, 2306.
72. D. Arigoni, O. Jeger, L. Ruzicka, Helv. Chim. Acta 1955, 38, 222.
73. D. H. R. Barton, Experientia 1950, 6, 316.
74. A. Fürst, P. A. Plattner, Helv. Chim. Acta 1949, 32, 275;
75. A. Fürst, P. A. Plattner, Abstracts of Papers, 12. Congress, IUPAC, NY, 1951, p. 409.
76. G. Gamboni, H. Schinz, A. Eschenmoser, Helv. Chim. Acta 1954, 37, 964.
77. P. A. Stadler, A. Nechvatal, A. J. Frey, A. Eschenmoser, Helv. Chim. Acta 1957, 40, 1373.
78. D. H. R. Barton, J. F. McGhie, M. K. Pradhan, S. A. Knight, Chem. Ind. (London) 1954, 1325.
79. G. M. Whitesides, C. P. Casey, J. K. Krieger, J. Am. Chem. Soc. 1971, 93, 1379;
80. D. Seyferth, L. G. Vaughan, J. Organomet. Chem. 1963, 1, 138.
81. V. Prelog, J. Chem. Soc. 1950, 420.
82. W. N. Haworth, 'The Constitution of Sugars', Arnold, London, 1929, p. 90.
83. F. Ebel, in 'Stereochemie', Ed. K. Freudenberg, Verlag F. Deutike, Leipzig/Wien, 1933, p. 825.
84. a) D. H. R. Barton Perspectives in Organic Chemistry on p. 68 and
85. b) V. Prelog on p. 96, in 'Perspectives in Organic Chemistry', Ed. A. Todd, Interscience Publishers, 1956.
86. E. J. Corey, J. J. Ursprung, J. Am. Chem. Soc. 1955, 77, 3668.
87. J. S. Mills, A. E. A. Werner, J. Chem. Soc. 1955, 3132.
88. J. B. Hendrickson, Tetrahedron 1959, 7, 82.
89. D. Arigoni, Pure Appl. Chem. 1975, 41, 219.
90. R. Rajamani, J. Gao, J. Am. Chem. Soc. 2003, 125, 12768.
91. S. Winstein, M. Shatavsky, C. Norton, R. B. Woodward, J. Am. Chem. Soc. 1955, 77, 4183.
92. R. P. Linstead, A. B. L. Wang, J. H. Williams, K. D. Errington, J. Chem. Soc. 1937, 1136;
93. R. P. Linstead, A. F. Millidge, A. L. Walpole, J. Chem. Soc. 1937, 1140.
94. G. Stork, H. Conroy, J. Am. Chem. Soc. 1951, 73, 4748.
95. A. W. Burgstahler, Thesis 1952, Harvard University.
96. C. Collin-Asselineau, M. E. Lederer, J. Polonsky, Bull. Soc. Chim. Fr. 1950, 17, 715.
97. P. A. Stadler, A. Eschenmoser, H. Schinz, G. Stork, Helv. Chim. Acta 1957, 40, 2191.
98. A. Eschenmoser, D. Felix, M. Gut, J. Meier, P. Stadler, Ciba Foundation Symposium on Biosynthesis of Terpenes and Sterols, 1959, p. 217.
99. W. S. Johnson, Acc. Chem. Res. 1968, 1, 1;
100. W. S. Johnson, Bioorg. Chem. 1976, 5, 51;
101. W. S. Johnson, Angew. Chem., Int. Ed. 1976, 15, 9.
102. W. S. Johnson, S. L. Gray, J. K. Crandall, D. M. Bailey, J. Am. Chem. Soc. 1964, 86, 1966.
103. L. D. Wright, E. L. Cresson, H. R. Skeggs, G. D. E. MacRae, C. H. Hoffman, D. E. Wolf, K. Folkers, J. Am. Chem. Soc. 1956, 78, 5273.
104. G. Tamura, J. Gen. Appl. Microbiol. 1956, 2, 431.
105. P. A. Tavormina, M. H. Gibbs, J. W. Huff, J. Am. Chem. Soc. 1956, 78, 4498.
106. M. Eberle, D. Arigoni, Helv. Chim. Acta 1960, 43, 1508.
107. J. W. Cornforth, Angew. Chem., Int. Ed. 1968, 7, 903.
108. T. T. Tchen, K. Bloch, J. Biol. Chem. 1957, 226, 931.
109. E. E. van Tamelen, J. D. Willett, R. B. Clayton, J. Am. Chem. Soc. 1967, 89, 3371.
110. a) S. Seo, A. Uomori, Y. Yoshimura, K. Takeda, H. Seto, Y. Ebizuka, H. Noguchi, U. Sankawa, J. Chem. Soc., Perkin Trans. 1 1988, 2407;
111. b) S. Seo, A. Uomori, Y. Yoshimura, K. Takeda, H. Seto, Y. Ebizuka, H. Noguchi, U. Sankawa, J. Chem. Soc., Perkin Trans. 1 1989, 261.
112. a) E. J. Corey, W. E. Russey, P. R. Ortiz de Montellano, J. Am. Chem. Soc. 1966, 88, 4750;
113. b) E. E. van Tamelen, J. D. Willett, R. B. Clayton, K. E. Lord, J. Am. Chem. Soc. 1966, 88, 4752.
114. D. H. R. Barton, T. R. Jarman, K. G. Watson, D. A. Widdowson, R. B. Boar, K. Damps, J. Chem. Soc., Chem. Commun. 1974, 861.
115. H. Suzuki, L. Achnine, R. Xu, S. P. T. Matsuda, R. A. Dixon, Plant J. 2002, 32, 1033.
116. R. K. Maudgal, T. T. Tchen, K. Bloch, J. Am. Chem. Soc. 1958, 80, 2589.
117. J. W. Cornforth, R. H. Cornforth, A. Pelter, M. G. Horning, G. Popjak, Tetrahedron 1959, 5, 311.
118. D. H. R. Barton, G. Mellows, D. A. Widdowson, J. J. Wright, J. Chem. Soc. C 1971, 1142 and refs. cit. therein.
119. W. O. Godtfredsen, W. von Daehne, S. Vangedal, A. Marquet, D. Arigoni, A. Melera, Tetrahedron 1965, 21, 3505.
120. A. Cooper, D. C. Hodgkin, Tetrahedron 1968, 24, 909.
121. a) T. G. Halsall, E. R. H. Jones, G. Lowe, C. E. Newall, J. Chem. Soc., Chem. Commun. 1966, 685;
122. b) P. Oxley, J. Chem. Soc., Chem. Commun. 1966, 729.
123. D. M. Crowfoot, B. W. Low, Br. J. Exp. Pathol. 1943, 24, 120.
124. a) T. Hattori, H. Igarashi, S. Iwasaki, S. Okuda, Tetrahedron Lett. 1969, 10, 1023;
125. b) A. Kawaguchi, H. Kobayashi, S. Okuda, Chem. Pharm. Bull. 1973, 21, 577.
126. E. J. Corey, S. C. Virgil, J. Am. Chem. Soc. 1991, 113, 4025.
127. E. J. Corey, S. C. Virgil, S. Sarshar, J. Am. Chem. Soc. 1991, 113, 8171.
128. G. Balliano, O. Caputo, F. Viola, L. Delprino, L. Cattel, Phytochemistry 1983, 22, 915.
129. D. Arigoni, Pure Appl. Chem. 1968, 17, 331.
130. D. Arigoni, Experientia 1958, 14, 153.
131. T. Koyama, K. Ogura, in 'Comprehensive Natural Products Chemistry, Vol. 2, Isoprenoids Including Carotenoids and Steroids', Ed. D. E. Cane, Elsevier, Amsterdam, 1999, p. 69-96.
132. a) T. Suga, T. Shishibori, S. Kimoto, Chem. Lett. 1972, 129, 313;
133. b) T. Suga, T. Shishibori, Phytochemistry 1975, 14, 2411.
134. B. Danieli, G. P. Forni, G. Palmisano, G. Rainoldi, G. Severini-Ricca, Chem. Ind. (London) 1974, 748.
135. H. G. Brunner, Ph.D. Thesis No. 5859, ETH-Zürich, 1976.
136. E. J. Corey, S. K. Gross, J. Am. Chem. Soc. 1968, 90, 5045.
137. S. Seo, Y. Tomita, K. Tori, J. Am. Chem. Soc. 1981, 103, 2075.
138. Q. Xiong, F. Rocco, W. K. Wilson, R. Xu, M. Ceruti, S. P. T. Matsuda, J. Org. Chem. 2005, 70, 5362.
139. A. Melera, D. Arigoni, A. Eschenmoser, O. Jeger, L. Ruzicka, Helv. Chim. Acta 1956, 39, 441.
140. E. J. Corey, E. W. Cantrall, J. Am. Chem. Soc. 1959, 81, 1745.
141. W. Angst, Ph.D. Thesis No. 6689, ETH-Zürich, 1980.
142. a) R. Giger, Ph.D. Thesis No. 5157, ETH-Zürich, 1973;
143. b) S. Seo, Y. Yoshimura, A. Uomori, K. Takeda, H. Seto, Y. Ebizuka, U. Sankawa, J. Am. Chem. Soc. 1988, 110, 1740.
144. K. Poralla, Chem. Biol. 2004, 11, 12.
145. E. Caspi, Acc. Chem. Res. 1980, 13, 97, and refs. cit. therein.
146. M. Rohmer, P. Bouvier, G. Ourisson, Eur. J. Biochem. 1980, 112, 557.
147. E. J. Corey, S. C. Virgil, H. Cheng, C. Hunter Baker, S. P. T. Matsuda, V. Singh, S. Sarshar, J. Am. Chem. Soc. 1995, 117, 11819.
148. T. Hoshino, T. Sato, Chem Commun. 2002, 291.
149. a) I. Abe, Y. Sakano, H. Tanaka, W. Lou, H. Noguchi, M. Shibuya, Y. Ebizuka, J. Am. Chem. Soc. 2004, 126, 3426;
150. b) A. Dietsch, Ph.D. Thesis, Université Louis Pasteur, Strasbourg, 1980.
151. O. Kennard, L. Riva di Sanseverino, J. S. Rollett, Tetrahedron 1967, 23, 131.
152. K. Nishimoto, M. Ito, S. Natori, T. Ohmoto, Tetrahedron 1968, 24, 735.
153. L. Jaenicke, F.-J. Marner, Pure Appl. Chem. 1990, 62, 1365.