Reserpine: A challenge for total synthesis of natural products

Chemical Reviews

Volumn 105, Issue 12, 2005, Pages 4671-4706

  Chen, Fen Er ^a   Huang, Jian ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CONDENSATION; CONFORMATIONS; MOLECULES; OXIDATION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); ZINC COMPOUNDS;

DIELS-ALDER CONDENSATION; NATURAL PRODUCTS; RADICAL CYCLIZATION; RESERPINE;

DRUG PRODUCTS;

BIOLOGICAL PRODUCT; RESERPINE;

CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; REVIEW; STEREOISOMERISM; SYNTHESIS;

BIOLOGICAL PRODUCTS; CYCLIZATION; MOLECULAR STRUCTURE; RESERPINE; STEREOISOMERISM;

EID: 30844451834     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr050521a     Document Type: Review

References (271)

1. Gaffrey, T. E.; Chidsey, C. A.; Braunwald, E. Circ. Res. 1963, 12, 264.
2. (a) Woodson, R. E.; Younken, H. W.; Schlittler, E.; Schneider, J. A. Rauwolfia: Botany, Pharmacognosy, Chemistry and Pharmacology; Little, Brown and Co.: Boston, 1957.
3. (b) Monachino, J. Econ. Bot. 1954, 8, 349.
4. (c) Chatterjee, A.; Pakrashi, S.; Werner, G. Fortschr. Chem. Org. Naturst. 1956, 13, 346.
5. (d) Lucas, R. A. Prog. Med. Chem. 1963, 3, 146.
6. (e) Physician's Desk Reference, 26th ed.; Medical Economics Inc.: 1972; p 659.
7. Schlitter, E. In The Alkaloids: Chemistry and Physiology; Manske, R. H. F., Ed.; Academic Press: New York, 1965; Vol. VIII, pp 287-334.
8. Muiler, J. M.; Schlittler, E.; Bein, H. J. Experientia 1952, 8, 338.
9. Dorfman, L.; Huebner, C. F.; MacPhillamy, H. B.; Schlittler, E.; Andre, A. F. St. Experientia 1953, 9, 368.
10. Aldrich, P. E.; Diassi, P. A.; Dickel, D. F.; Dylion, C. M.; Hance, P. D.; Huebner, C. F.; Korzun, B.; Kuehne, M. E.; Liu, L. H.; MacPhillamy, H. B.; Robb, E. W.; Roychaudhuri, D. K.; Schlittler, E.; André, A. F. S.; van Tamelen, E. E.; Weisenborn, F. L.; Wenkert, E.; Wintersteiner, O. J. Am. Chem. Soc. 1959, 81, 2481.
11. Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. Tetrahedron 1958, 2, 1.
12. Karle, I. L.; Karle, J. Acta Crystallogr. B 1968, 24, 81.
13. Huebner, C. F.; MacPhillamy, H. B.; Schlittler, E.; Andre, A. F. St. Experientia 1955, 11, 303.
14. Diassi, P. A.; Weisenborn, F. L.; Dylion, C. M.; Wintersteiner, O. J. Am. Chem. Soc. 1955, 77, 2028.
15. (a) Klyne, W. Chem. Ind. 1953, 1032.
16. (b) Klyne, W. Chem. Ind. 1954, 1198.
17. Ban, Y.; Yonemitsu, O. Tetrahedron 1964, 20, 2877.
18. Barger, G.; Scholz, C. Helv. Chem. Acta. 1933, 16, 1343.
19. Hahn, G.; Werner, H. Justus Liebigs Ann. Chem. 1935, 520, 123.
20. Woodward, R. B. Angew. Chem. 1956, 68, 13.
21. Wenkert, E.; Bringi, N. V. J. Am. Chem. Soc. 1959, 81, 1474.
22. Leete, E. J. Am. Chem. Soc. 1960, 82, 6338.
23. (a) Cordell, G. A. Introduction to Alkaloids: A biogenic Approach; Wiley: New York, 1981.
24. (b) Dalton, D. The Alkaloids, The Fundamental Chemistry, A Biogenic Approach; Marcel Dekker: New York, 1979.
25. (a) Sakai, S.; Ogawa, M. Chem. Pharm. Bull. 1978, 26, 678.
26. (b) Sakai, S.; Ogawa, M. Heterocycles 1978, 10, 67.
27. Klohs, M. W.; Draper, M. D.; Keller, F.; Petracek, F. J. J. Am. Chem. Soc. 1953, 75, 4867.
28. (a) Szalkowski, C. R.; Mader, W. J. J. Am. Pharm. Assoc. (Sci. Ed.) 1956, 45, 613.
29. (b) Banes, D.; Wolff, J.; Fallscheer, H. O.; Carol, J. J. Am. Pharm. Assoc. (Sci. Ed.) 1956, 45, 710.
30. The United States Pharmacopeia, 21st rev.; U. S. pharmacopeial Convention, Inc.: Rockville, MD, 1985; p 935.
31. Awang, D. V. C.; Dawson, B. A.; Girard, M.; Vincent, A. J. Org. Chem. 1990, 55, 4443.
32. For some authoritative monographs, see: (a) Nicolaou, K. C.; Sorensen, L. E. In Classic in Organic Synthesis; VCH: New York, 1996.
33. (b) Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; Wiley: New York, 1989.
34. (c) In Strategies and Tactics in Organic Synthesis; Lindberg, T., Ed.; Academic: San Diego, CA, 1991; Vols. 1-3.
35. (d) Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, The Netherlands, 1994; Vols. 1-14.
36. Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023.
37. Wender, P. A.; Schaus, J. M.; White, A. W.J. Am. Chem. Soc. 1980, 102, 6157.
38. (a) Aube, J.; Ghosh, S. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, pp 99-150.
39. (b) Baxter, E. W.; Mariano, P. S. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Springer-Verlag: New York, 1992: Vol. 8, pp 197-319.
40. (c) Szantay, C.; Honty, K. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; John Wiley & Sons: Chichester, 1994; Chapter 4, pp 161-216.
41. (d) Szantay, C.; Blasko, G.; Honty, K.; Dornyei, G. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, FL, 1986; Vol. 27, pp 131-268.
42. For reviews, see: (a) Ashby, E. C. Acc. Chem. Res. 1988, 21, 414.
43. (b) Aremo, N.; Hase, T. Org. React. 2001, 42, 3637.
44. Akabori, S.; Saito, K. Ber. Dtsch. Chem. Ges. 1930, 63, 2245.
45. For similar cyclization, see: (a) Bischler, A.; Napieralski, B. Ber. Dtsch. Chem. Ges. 1893, 26, 1903.
46. (b) Fodor, G.; Nagubandi, S. Heterocycles 1981, 15, 165.
47. (c) Marquart, A. L.; Podlogar, B. L.; Huber, E. W.; Demeter, D. A.; Peet, N. P.; Weintraub, H. J. R.; Angelastro, M. R. J. Org. Chem. 1994, 59, 2092.
48. (d) Sotomayor, N.; Dominguez, E.; Lete, E. J. Org. Chem. 1996, 61, 4062.
49. (e) Rozwadowska, M. D. Heterocycles 1994, 39, 903.
50. (f) Doi, S.; Shirai, N.; Sate, Y. J. Chem. Soc., Perkin Trans. 1 1997, 2217.
51. (g) Sanchez-Sancho, F.; Mann, E.; Herradon, B. Synlett 2000, 509.
52. (h) Miyatani, K.; Ohno, M.; Tatsumi, K.; Ohishi, Y.; Kunitomo, J.-I.; Kawasaki, I.; Yamashita, M.; Ohta, S. Heterocycles 2001, 55, 589.
53. (i) Nicoletti, M.; O'Hagan, D.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 2002, 116.
54. Woodward, R. B.; Bader, F. E.; Bickel, H.; Fery, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2657.
55. Li, Y.-Y.; Xu, M.; Chen, F.-E. Chin. Chem. Lett. 2004, 15, 265.
56. Weichet, J.; Pelz, K.; Blaha, L. Collect. Czech. Chem. Commun. 1961, 26, 1529.
57. Velluz, L.; Muller, G.; Joly, R.; Nomine, G.; Mathieu, J.; Allais, A.; Warnant, J.; Valls, J.; Bucourt, R.; Jolly, J. Bull. Soc. Chim. Fr. 1958, 673.
58. (a) Novak, L.; Jilek, J. O.; Kakac, B.; Protiva, M. Tetrahedron Lett. 1959, 10.
59. (b) Novak, L.; Jilek, J. O.; Kakac, B.; Protiva, M. Collect. Czech. Chem. Commun. 1960, 25, 2196.
60. Woodward, R. B. U.S. Patent 2,883,384, Apr 21, 1959
61. Chem. Abstr. 1959, 53, 20118h.
62. Muller, G.; Marne, N.; Nomine, G.; le Sec, N.; Warnant, J.; Seine, N. U.S. Patent 2,952,682, Sept 13, 1960;
63. Muller, G.; Marne, N.; Nomine, G.; le Sec, N.; Warnant, J.; Seine, N. Chem. Abstr. 1961, 55, 17679a.
64. Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6404.
65. For reviews, see: (a) de Mayo, P. Acc. Chem. Res. 1971, 4, 49.
66. (b) Oppolzer, W. Pure Appl. Chem. 1981, 53, 1189.
67. Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6398.
68. (a) Kuehne, M. E.; Lambert, B. F. Org. Synth. 1973, 5, 400.
69. (b) Camps, F.; Coll, J.; Pascual, J. J. Org. Chem. 1967, 32, 2563.
70. Binsch, G. The Study of Intramolecular Rate Processes by Dynamic Nuclear Magnetic Resonance. Top. Stereochem. 1968, 3, 97.
71. Fuchs, G.; Hellstrom, N. Lantbrukshoegsk. Ann. 1964, 30, 615; Chem. Abstr. 1965, 63, 6850g.
72. Fuchs, G.; Hellstrom, N. Chem. Abstr. 1965, 63, 6850g.
73. Robson, R.; Grubb, P. W.; Barltrop, J. A. J. Chem. Soc. 1964, 2153.
74. Emmons, W. D.; Lucas, G. B. J. Am. Chem. Soc. 1955, 77, 2287.
75. Stork, G. Pure Appl. Chem. 1989, 61, 439.
76. For representative examples, see: (a) Ihara, M.; Suzuki, M.; Fukumoto, K.; Kametani, T.; Kabuto, C. J. Am. Chem. Soc. 1988, 110, 1963.
77. (b) Ihara, M.; Suzuki, M.; Fukumoto, K.; Kabuto, C. J. Am. Chem. Soc. 1990, 112, 1164.
78. (c) Ihara, M.; Makita, K.; Fujiwara, Y.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 6416.
79. (d) Hughes, F., Jr.; Grossman, R. B. Org. Lett. 2001, 3, 2911.
80. (e) Holeman, D. S.; Rasne, R. M.; Grossman, R. B. J. Org. Chem. 2002, 67, 3149.
81. For reviews, see: (a) Mori, A.; Inane, S. Compr. Asymmetric Catal. I-III 1999, 2, 983.
82. (b) Groger, H. Chem. Rev. 2003, 103, 2795.
83. Due to the absence of reaction conditions in the original literature, the reaction conditions a-f come from the following: Toyata, M.; Asoh, T.; Matsuura, M.; Fukumote, K. J. Org. Chem. 1996, 61, 8687.
84. Reaction conditions g are referred to the following: Ihara, M.; Suzuki, M.; Fukumoto, K.; Kametani, T.; Kabuto, C. J. Am. Chem. Soc. 1988, 110, 1963.
85. Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3095.
86. For representative examples, see: (a) Tamao, K.; Akita, H.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983.
87. (b) Tamao, K.; Ishida, N.; Kumada, M. J. Org. Chem. 1983, 48, 2120.
88. (c) Fleming, I.; Henning, R.; Plant, H. J. Chem. Soc., Chem. Commun. 1984, 29.
89. (d) Kim, S.; Emeric, G.; Fuchs, P. L. J. Org. Chem. 1992, 57, 7362.
90. (e) Jones, G. R.; Landais, Y. Tetrahedren 1996, 52, 7599.
91. (f) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112.
92. (g) Knolker, H.-J.; Jones, P. G.; Wanzl, G. Synlett 1997, 613.
93. (h) Studer, A.; Steen, H. Chem. Eur. J. 1999, 5, 759.
94. (i) Barrett, A. G. M.; Head, J.; Smith, M. L.; Stork, N. S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1999, 64, 6005.
95. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983.
96. (a) Gomez, A. M.; Lepez, J. C.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 4048.
97. (b) Gomez, A. M.; Lopez, J. C.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3859.
98. Ferrier, R. J.; Prasad, N. J. Chem. Soc. C 1969, 570.
99. Gomez, A. M.; Lopez, J. C.; Fraser-Reid, B. J. Chem. Soc., Perkin Trans. 1 1994, 1689.
100. (a) Russell, G. A. Acc. Chem. Res. 1989, 22, 1.
101. (b) Russell, G. A.; Ngoviwatchai, P. Tetrahedron Lett. 1985, 26, 4975.
102. (c) Russell, G. A.; Tashtoush, H.; Ngoviwatchai, P. J. Am. Chem. Soc. 1984, 106, 4622.
103. (a) Baldwin, J. E.; Kelly, D. R. J. Chem. Soc., Chem. Commun. 1985, 682.
104. (b) Baldwin, J. E.; Kelly, D. R.; Ziegler, C. B. J. Chem. Soc., Chem. Commun. 1984, 133.
105. Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298.
106. (a) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500.
107. (b) Stork, G.; Sofia, M. J. J. Am. Chem. Soc. 1986, 108, 6826.
108. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303.
109. (a) David, S. C. R. Sci. Paris, Ser. C 1974, 278, 1051.
110. (b) David, S.; Thieffry, A. J. Chem. Soc., Perkin Trans. 1 1979, 1568.
111. (c) Kong, X.; Grindley, T. B. J. Carbohydr. Chem. 1993, 12, 557.
112. (a) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273.
113. (b) Turnbull, M. D.; Hatter, G.; Ledgerwood, D. E. Tetrahedron Lett. 1964, 25, 5449.
114. (a) Levine, S. G. J. Am. Chem. Soc. 1958, 80, 6150.
115. (b) Earnshaw, C.; Wallis, C. J.; Warren, S. J. Chem. Soc., Chem. Commun. 1977, 314.
116. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 399.
117. Hashimoto, N.; Aoyama, T.; Shiori, T. Chem. Pharm. Bull. 1981, 29, 1475.
118. 5,6eq=5.1.
119. Chu, C.-S.; Liao, C.-C.; Rao, P. D. J. Chem. Soc., Chem. Commun. 1996, 1537.
120. For reviews, see: (a) Ciganek, E. Org. React. 1984, 32, 1.
121. (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990; p 140.
122. Chu, C.-S.; Lee, T.-H.; Liao, C.-C. Synlett 1994, 635.
123. (a) Tamura, Y.; Yakura, T.; Haruta, J. I.; Kita, Y. J. Org. Chem. 1987, 52, 3927.
124. (b) Tamura, Y.; Yakura, T.; Tohma, H.; Kikuchi, K.; Kita, Y. Synthesis 1989, 126.
125. Lewis, N.; Wallbank, P. Synthesis 1987, 1103.
126. 2 in organic synthesis, see: (a) Dahlen, A.; Hilmersson, G. Eur. J. Inorg. Chem. 2004, 3393.
127. (b) Molander, G. A. Chem. Rev. 1992, 92, 29.
128. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
129. (d) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745.
130. (e) Molander, G. A. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, pp 153-182.
131. For selected examples of the use of(-)-quinic acid as a starting material and chiral template, see: (a) Fernandez, S.; Diaz, M.; Ferrero, M.; Gotor, V. Tetrahedron Lett. 1997, 38, 5225.
132. (b) Barco, A.; Benetti, S.; De Risi, C.; Marchetti, P.; Pollini, G. P.; Zanirate, V. Tetrahedron: Asymmetry 1998, 9, 2857.
133. (c) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749.
134. (d) Shih, T.-L.; Wu, S.-H. Tetrahedron Lett. 2000, 41, 2957.
135. (e) Usami, Y.; Hatsuno, C.; Yamamoto, H.; Tanabe, M.; Numata, A. Chem. Pharm. Bull. 2004, 52, 1130.
136. For a review on the use of (-)-quinic acid as a chiron store for natural product synthesis, see: Barco, A.; Benetti, S.; Risi, C. D.; Marchetti, P.; Pollini, G. P.; Zanirate, V. Tetrahedron: Asymmetry 1997, 8, 3515.
137. Hanessian, S.; Pan, J.; Carnell, A.; Bouchard, H.; Lesage, L. J. Org. Chem. 1997, 62, 465.
138. Philippe, M.; Sepulchre, A. M.; Gero, S. D.; Loibner, H.; Streicher, W.; Stutz, P. J. Antibiot. 1982, 35, 1507.
139. Wagner, D.; Verheyden, J.; Moffatt, J. G. J. Org. Chem. 1974, 39, 24.
140. (a) Roush, W. R.; Michaelides, M. R.; Tai, D. F.; Lesur, B. M.; Chong, W. K. M.; Harris, D. J. J. Am. Chem. Soc. 1989, 111, 2984.
141. (b) Bliard, C.; Herczegh, P.; Olesker, A.; Lukacs, G. J. Carbohydr. Chem. 1989, 8, 103.
142. (c) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643.
143. Pearlman, W. M. Tetrahedron Lett. 1967, 1663.
144. For an early example of ether-directed attack of Grignard reagents, see: (a) Wolfrom, M. L.; Hanessian, S. J. Org. Chem. 1962, 27, 1800.
145. (b) Still, W. C.; McDonald, J. H. Tetrahedron Lett. 1980, 21, 1031.
146. (c) Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748.
147. Hanessian, S.; DiFabio, R.; Prud'Homme, M.; Marcoux, J.-F. J. Org. Chem. 1990, 55, 3436.
148. See also: (a) Nagai, Y.; Matsumoto, H.; Kayama, M.; Nakano, T. Chem. Lett. 1981, 415.
149. (b) Kraus, G. A.; Landgrebe, K. Tetrahedron Lett. 1984, 25, 3939.
150. (c) Belletire, J. L.; Mahmoodi, N. O. Tetrahedron Lett. 1989, 30, 4363.
151. (d) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
152. For the application of organoboranes as a source of radical, see: (a) Ollivier, C.; Renaud, P. Chem. Rev. 2001, 101, 3415.
153. (b) Hiroyuki, I.; Masatake, I.; Masashi, O.; Masazumi, I. Tetrahedron Lett. 1999, 40, 1149.
154. Brown, H. C. Boranes in Organic Chemistry; Cornell University Press: Ithaca, NY, 1972.
155. For a review, see: Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
156. (a) Mehta, G.; Reddy, D. S. Synlett 1997, 612.
157. (b) Mehta, G.; Reddy, D. S. J. Chem. Soc., Perkin Trans. 1 1998, 2125.
158. Mehta, G.; Reddy, D. S. J. Chem. Soc., Perkin Trans. 1 2000, 1399.
159. Peri, C. A. Gazz. Chim. Ital. 1955, 85, 1118.
160. Rao, H. S. P.; Senthilkumar, S. P.; Reddy, D. S.; Mehta, G. Indian J. Chem. 1999, 38B, 260.
161. Wender, P. A.; Schaus, J. M.; Torney, D. C. Tetrahedron Lett. 1979, 20, 2485.
162. For reviews, see: (a) Hill, R. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 5, p 785.
163. (b) Davies, H. M. L. Tetrahedron 1993, 49, 5203.
164. (c) Paquette, L. A. Tetrahedron 1997, 53, 13971.
165. (d) Miyashi, T.; Ikeda, H.; Takahashi, Y. Acc. Chem. Res. 1999, 32, 815.
166. (e) Nakamura, H.; Yamamoto, Y. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: New York, 2002; Vol. 2, p 2919.
167. Fowler, F. W. J. Org. Chem. 1972, 37, 1321.
168. Hassner, A.; Krepski, L.; Alexanian, V. Tetrahedron 1978, 34, 2069.
169. Eistert, B.; Arndt, F.; Loewe, L.; Ayca, A. Ber. 1951, 84, 156.
170. (a) Jung, M. E.; Lyster, M. A. J. Am. Chem. Soc. 1977, 99, 968.
171. (b) Jung, M. E.; Lyster, M. A. J. Chem. Soc., Chem. Commun. 1978, 315.
172. For examples of similar cyclizations, see: (a) Wenkert, E.; Wickberg, B. J. Am. Chem. Soc. 1962, 84, 4914.
173. (b) Morrison, G. C.; Cetenko, W.; Shavel, J., Jr. J. Org. Chem. 1967, 32, 4089.
174. (c) Gutzwiller, J.; Pizzolato, G.; Uskokovic, M. J. Am. Chem. Soc. 1971, 93, 5908.
175. (d) Stork, G.; Guthikonda, N. J. Am. Chem. Soc. 1972, 94, 5110.
176. (e) Aimi, N.; Yamanaka, E.; Endo, J.; Sakai, S.; Haginiwa, J. Tetrahedron Lett. 1972, 1081.
177. (f) Aimi, N.; Yamanaka, E.; Endo, J.; Sakai, S.; Haginiwa, J. Tetrahedron 1973, 29, 2015.
178. (g) Husson, H.-P.; Chevolot, L.; Langlois, Y.; Thal, C.; Potier, P. J. Chem. Soc., Chem. Commun. 1972, 930.
179. (h) Sakai, S.; Aimi, N.; Endo, J.; Shimizu, M.; Yamanaka, E.; Katano, K.; Kashiwazaki, M.; Fujiu, M.; Yamamato, Y. Yakugaku Zasshi 1978, 98, 850.
180. (i) Gutzwiller, J.; Pizzelato, G.; Uskokovic, M. R. Helv. Chim. Acta. 1981, 64, 1663.
181. (j) Fujii, T.; Ohba, M.; Sasaki, N. Heterocycles 1984, 22, 1805.
182. (k) Sakai, S.; Ogawa, M. Chem. Pharm. Bull. 1978, 26, 678.
183. (l) Sakai, S.; Ogawa, M. Heterocycles 1978, 10, 67.
184. Inside reserpinediol is that product which arises from cyclization of the iminium salt derived by oxidation of 149 at C-21.
185. (a) Huebner, C. F.; Kuehne, M. E.; Korzun, B.; Schlittler, E. Experientia 1956, 12, 249.
186. (b) Weisenborn, F. L.; Diassi, P. A. J. Am. Chem. Soc. 1956, 78, 2022.
187. (c) Huebner, C. F. U.S. Patent 2,957,877, Oct 25, 1960;
188. Huebner, C. F. Chem. Abstr. 1961, 55, 5565b.
189. Wender, P. A.; Schaus, J. M.; White, A, W. Heterocycles 1987, 25, 263.
190. 18β alcohol (α:β=73:27).
191. (a) Martin, S. F.; Grzejszczak, S.; Rueger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072.
192. (b) Martin, S. F.; Rueger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124.
193. Martin, S. F.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1983, 48, 5170.
194. Martin, S. F.; Benage, B.; Williamson, S. A.; Brown, S. P. Tetrahedron 1986, 42, 2903.
195. Wiley, R. H.; Hart, A. J. J. Am. Chem. Soc. 1954, 76, 1942.
196. 3.
197. (a) Shea, K. J.; Svoboda, J. J. Tetrahedron Lett. 1986, 27, 4837.
198. (b) Gutierrez, A. J.; Shea, K. J.; Svoboda, J. J. J. Org. Chem. 1989, 54, 4335.
199. (c) Sparks, S. M.; Shea, K. J. Tetrahedron Lett. 2000, 41, 6721.
200. Sparks, S. M.; Shea, K. J. Org. Lett. 2001, 3, 2265.
201. For a review, see: Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
202. Paterson, I.; Fessner, K.; Finlay, M. R. V.; Jacobs, M. F. Tetrahedron Lett. 1996, 37, 8803.
203. Weir, J. R.; Patel, B. A.; Heck, R. F. J. Org. Chem. 1980, 45, 4926.
204. Greico, P. A.; Yoshida, K.; He, A. Tetrahedron Lett. 1984, 25, 5715.
205. Bald, E.; Saigo, Z.; Mukaiyama, T. Chem. Lett. 1975, 1163.
206. Cycloaddition in refiuxing benzene gave a lower endo/exo ratio (4:1).
207. Baxter, E. W.; Labaree, D.; Ammon, H. L.; Mariano, P. S. J. Am. Chem. Soc. 1990, 112, 7682.
208. Sparks, S. M.; Gutierrez, A. J.; Shea, K. J. J. Org. Chem. 2003, 68, 5274.
209. Zhang, H. X.; Guibe, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857.
210. Heathcock, C. H.; Stafford, J. A.; Clark, D. L. J. Org. Chem. 1992, 57, 2575.
211. For representative examples, see: (a) Wenkert, E.; Liu, L. H.; Johnston, D. B. R. J. Org. Chem. 1965, 30, 722.
212. (b) Wenkert, E. Heterocycles 1984, 21, 325.
213. (c) Takano, S.; Ito, F.; Ogasawara, K. Heterocycles 1980, 14, 453.
214. (d) Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Chem. Pharm. Bull. Jpn. 1981, 29, 76.
215. (e) Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Heterocycles 1980, 14, 439.
216. (f) Chao, S.; Kunng, F.-A.; Gu, J.-M.; Ammon, H. L.; Mariano, P. S. J. Org. Chem. 1984, 49, 2708.
217. (g) Jung, M. E.; Light, L. A. J. Am. Chem. Soc. 1984, 106, 7614.
218. (h) Isobe, M.; Fukami, N.; Nishikawa, T.; Goto, T. Heterocycles 1987, 25, 521.
219. (i) Polniaszek, R. P.; Stevens, R. V. J. Org. Chem. 1986, 51, 3023.
220. (j) Szantay, C.; Blasko, G.; Honty, K.; Baitz-Gacs, E.; Tamas, J.; Toke, L. Justus Liebigs Ann. Chem. 1983, 1292.
221. (k) Miyata, O.; Hirata, Y.; Naito, T.; Ninomiya, I. Heterocycles 1984, 22, 1041.
222. (l) Stevens, R. V.; Moran, J. R. ACS/CJS Chemical Congress, April 1-6, 1979; ORGN 289.
223. (m) Szantay, C.; Blasko, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1269.
224. (n) Kunng, F.-A.; Gu, J.-M.; Chao, S.; Chen, Y.; Mariano, P. S. J. Org. Chem. 1983, 48, 4262.
225. (o) Kametani, T.; Suzuik, T.; Tomino, A.; Unno, K. Chem. Pharm. Bull. 1982, 30, 167.
226. (p) Baxter, E. W.; Labaree, D.; Chao, S.; Mariano, P. S. J. Org. Chem. 1989, 54, 2893.
227. (q) Toyota, M.; Matsuura, M.; Fukumoto, K. Heterocycles 1995, 41, 661.
228. (r) Toyota, M.; Wada, T.; Matsuura, M.; Fukumoto, K. Synlett 1995, 761.
229. Studies on asymmetric total synthesis of L-reserpine via an asymmetric catalytic Diels-Alder reaction between 1,4-benzo-quinone and a modified diene are now in progress in our laboratory.
230. Aube, J.; Ghosh, S.; Tanol, M. J. Am. Chem. Soc. 1994, 116, 9009.
231. (a) Hirai, Y.; Terada, T.; Yamazaki, T.; Momose, T. Tetrahedron Lett. 1990, 31, 4755.
232. (b) Hirai, Y.; Terada, T.; Yamazaki, T.; Momose, T. J. Chem. Soc., Perkin Trans. 1 1992, 517.
233. Kuehne, M. E.; Muth, R. S. J. Org. Chem. 1991, 56, 2701.
234. Wenkert, E.; Pyrek, J. S.; Uesato, S.; Vankar, Y. D. J. Am. Chem. Soc. 1982, 104, 2244.
235. Stork, G.; Guthikonda, R. N. J. Am. Chem. Soc. 1972, 94, 5109.
236. Blasko, G.; Knight, H.; Honty, K.; Szantay, C. Liebigs Ann. Chem. 1986, 655.
237. (a) Kametani, T.; Hirai, Y.; Fukumoto, K. Chem. Pharm. Bull. 1976, 24, 2500.
238. (b) Kametani, T.; Hirai, Y.; Fukumoto, K. Heterocycles 1976, 4, 29.
239. Wenkert, E.; Halls, T. D. J.; Kunesch, G.; Orito, K.; Stephens, R. L.; Temple, W. A.; Yadv, J. S. J. Am. Chem. Soc. 1979, 101, 5370.
240. (a) Kametani, T.; Hirai, Y.; Kajiwara, M.; Takahashi, T.; Fukumoto, K. Chem. Pharm. Bull. 1975, 23, 2634.
241. (b) Kametani, T.; Kajiwara, M.; Takahashi, T.; Fukumote, K. Heterocycles 1975, 3, 179.
242. Szantay, C.; Honty, K.; Toke, L.; Buzas, A.; Jacquet, J. P. Tetrahedron Lett. 1971, 4871.
243. Toke, L.; Honty, K.; Szantay, C. Chem. Ber. 1969, 102, 3248.
244. Szantay, C.; Toke, L.; Honty, K. Tetrahedron Lett. 1965, 1665.
245. (a) van Tamelen, E. E.; Shamma, M.; Burgstahler, A. W.; Wolinsky, J.; Tamm, R.; Aldrich, P. E. J. Am. Chem. Soc. 1958, 80, 5006.
246. (b) van Tamelen, E. E.; Shamma, M.; Burgstahler, A. W.; Wolinsky, J.; Tamm, R.; Aldrich, P. E. J. Am. Chem. Soc. 1969, 91, 7315.
247. Szantay, C.; Honty, K.; Toke, L.; Szabo, L. Chem. Ber. 1976, 109, 1737.
248. Miyata, O.; Hirata, Y.; Naito, T.; Ninomiya, I. J. Chem. Soc., Chem. Commun. 1983, 1231.
249. Brown, R. T.; Pratt, S. B.; Richards, P. Tetrahedron Lett. 2000, 41, 5627.
250. Naito, T.; Hirata, Y.; Miyata, O.; Ninomiya, I.; Inoue, M.; Kamiichi, K.; Doi, M. Chem. Pharm. Bull. 1989, 37, 901
251. Szantay, C.; Blasko, G.; Honty, K.; Szabo, L.; Toke, L. Heterocycles 1977, 7, 155.
252. Wenkert, E.; Kunesch, G.; Orito, K.; Temple, W. A.; Yadav, J. S. J. Am. Chem. Soc. 1978, 100, 4894.
253. Brown, R. T.; Danda, B. E. N.; Pratt, S. B.; Richards, P. Heterocycles 2002, 56, 51.
254. Logers, M.; Overman, L. E.; Welmaker, G. S. J. Am. Chem. Soc. 1995, 117, 9139.
255. Honda, T.; Haze, N.; Ishige, H.; Masnda, K.; Naito, K.; Suzuki, Y. J. Chem. Soc., Perkin Trans. 1 1993, 539.
256. Hanessian, S.; Faucher, A.-M. J. Org. Chem. 1991, 56, 2947.
257. Takano, S.; Satoh, S.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1988, 59.
258. Naito, T.; Kojima, N.; Miyata, O.; Ninomiya, I. Heterocycles 1986, 24, 2117.
259. Massiot, G.; Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715.
260. Jarreau, F.-X.; Goutarel, R. Tetrahedron 1975, 31, 2695.
261. Martin, S. F.; Clark, C. W.; Corbett, J. W. J. Org. Chem. 1995, 60, 3236.
262. Hatakeyama, S.; Saijo, K.; Takano, S. Tetrahedron Lett. 1985, 26, 865.
263. Gutzwiller, J.; Pizzolato, G.; Uskokovic, M. J. Am. Chem. Soc. 1971, 93, 5907.
264. Winterfeldt, E.; Radunz, H.; Korth, T. Chem. Ber. 1968, 101, 3172.
265. Winterfeldt, E.; Gaskell, A. J.; Korth, T.; Radunz, H.-E.; Walkowiak, M. Chem. Ber. 1969, 102, 3558.
266. (a) van Tamelen, E. E.; Placeway, C. J. Am. Chem. Soc. 1961, 83, 2594.
267. (b) van Tamelen, E. E.; Placeway, C.; Schiemenz, G. P.; Wright, I. G. J. Am. Chem. Soc. 1969, 91, 7359.
268. Martin, S. F.; Rueger, H. Tetrahedron Lett. 1985, 26, 5227.
269. Honty, K.; Baitz-Gacs, E.; Blasko, G.; Szantay, C. J. Org. Chem. 1982, 47, 5111.
270. (a) Toke, L.; Honty, K.; Szabo, L.; Blasko, G.; Szantay, C. J. Org. Chem. 1973, 38, 2496.
271. (b) Toke, L.; Gombos, Z.; Blasko, G.; Honty, K.; Szabo, L. J. Org. Chem. 1973, 38, 2501.