Alkaloid Synthesis

The Total Synthesis of Natural Products

Volumn 3, Issue , 2007, Pages 439-554

  Stevens, R V ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Crinine type alkaloids; Hexahydrojulolidine chemistry; Lycorine type alkaloids; Mesembrine alkaloids; Pyrrolizidine alkaloids

Indexed keywords

EID: 84995479234     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470129661.ch3     Document Type: Chapter

References (296)

1. E. J. Corey and T. Wipke, Science, 166, 179 (1969).
2. A. Popelak and G. Lettenbauer, The Alkaloids, 9, 467 (1967).
3. P. W. Jeffs, R. L. Hawks, and D. S. Farrier, J. Amer. Chem. Soc., 91, 3831 (1969).
4. P. W. Jeffs, G. Ahmann, H. F. Campbell, D. S. Farrier, G. Ganguli, and R. L. Hawks, J. Org. Chem., 35, 3512 (1970).
5. R. R. Arndt and P. E. J. Kruger, Tetrahedron Lett., 3237 (1970).
6. A. Popelak, G. Lettenbauer, E. Haack, and H. Spingler, Naturwissenschaften, 47, 231 (1960).
7. M. Shamma and H. R. Rodriguez, Tetrahedron, 24, 6583 (1968); Tetrahedron Lett., 4847(1965).
8. W. C. Wildman, J. Amer. Chem. Soc., 78, 4180 (1956).
9. H. W. Whitlock, Jr., and G. L. Smith, J. Amer. Chem. Soc., 89, 3600 (1967); Tetrahedron Lett., 1389 (1965); 2711 (1966).
10. L. Raiford and D. Fox, J. Org. Chem., 9, 170 (1944).
11. W. C. Wildman and R. B. Wildman, J. Org. Chem., 17, 581 (1952).
12. R. Pappo, D. S. Allen, Jr., R. V. Lemieux, and W. S. Johnson, J. Org. Chem., 28, 250 (1963).
13. A. Marwuet and J. Jacques, Tetrahedron Lett., 24 (1959).
14. S. Marmor, J. Org. Chem., 28, 250 (1963).
15. P. L. Julian, W. Cole, E. W. Meyer, and B. M. Regan, J. Amer. Chem. Soc., 77, 4601 (1955).
16. R. V. Stevens and M. P. Wentland, J. Amer. Chem. Soc., 90, 5580 (1968); Tetrahedron Lett., 2613 (1968).
17. C. Dupin and R. Fraisse-Julien, Bull. Soc. Chim. France, 1993 (1964).
18. D. I. Schuster and J. D. Roberts, J. Org. Chem., 27, 51 (1962).
19. S. L. Keely, Jr., and F. C. Tahk, J. Amer. Chem. Soc., 90, 5584 (1968); Chem. Comm., 441 (1968).
20. T. J. Curphey and H. L. Kim, Tetrahedron Lett., 1441 (1968).
21. E. A. Prill and S. M. McElvain, J. Amer. Otem. Soc., 55, 1233 (1933).
22. J. M. Bruce, J. Chem. Soc., 2366 (1959).
23. F. H. Howell and D. H. Taylor, J. Otem. Soc., 4252 (1956).
24. T. Oh-ishi and H. Kugita, Chem. Pharm. Bull. (Japan), 18, 291, 299 (1970); Tetrahedron Lett., 5445 (1968).
25. C. F. Koelsch and H. M. Walker, J. Amer. Chem. Soc., 72, 346 (1950).
26. C. F. Koelsch and D. L. Ostercamp, J. Org. Chem., 26, 1104 (1961).
27. Y. Ban, Y. Sato, I. Inoue, M. Nagai, T. Oishi, M. Terashima, O. Yonemitsu, and K. Kanaoka, Tetrahedron Lett., 2261 (1965).
28. H. Taguchi, T. Oh-ishi, and H. Kugita, Chem. Pharm. Bull. (Japan), 18, 1008 (1970); Tetrahedron Lett., 5763 (1968).
29. R. V. Stevens and J. T. Lai, J. Org. Chem., 37, 2138 (1972).
30. W. C. Wildman, The Alkaloids, 6, 289 (1960); 11, 307 (1968).
31. W. C. Wildman and L. H. Mason, J. Amer. Chem. Soc., 76, 6194 (1954).
32. H. Muxfeldt, R. S. Schneider, and J. B. Mooberry, J. Amer. Chem. Soc., 88, 3670 (1966).
33. T. Kametani and H. Ida, J. Pharm. Soc. Japan, 73, 681 (1953).
34. H. Muxfeldt, Angew. Chem., 74, 825 (1962).
35. H. Meerwein, W. Florian, N. Schön, and G. Stopp, Annalen, 641, 1 (1961).
36. A. E. Wick, D. Felix, K. Steen, and A. Eschenmose, Helv. Chim. Acta, 47, 2425 (1964).
37. W. C. Wildman, J. Amer. Chem. Sc., 80, 2567 (1958).
38. H. Born, R. Pappo, and J. Szmuszkovicz, J. Chem. Soc., 1779 (1953).
39. R. O. Clinton and S. C. Laskowski, J. Amer. Chem. Soc., 70, 135 (1948).
40. H. W. Heine, J. Amer. Chem. Soc., 85, 2743 (1963).
41. H. M. Fales and W. C. Wildman, J. Org. Chem., 26, 881 (1961).
42. H. Goering, Rec. Chem. Progr., 21, 109 (1960).
43. S. Uyeo, H. Irie, A. Yoshitake, and A. Ito, Chem. Pharm. Butt. (Tokyo), 13, 427 (1965).
44. H. Irie, Y. Tsuda, and S. Uyeo, J. Chem. Soc., 1446 (1959).
45. W. S. Wadsworth, Jr., and W. D. Emmons, J. Amer. Chem. Soc., 83, 1773 (1961).
46. H. Irie, S. Uyeo, and A. Yoshitake, J. Chem. Soc. (C) 1802 (1968); Chem. Comm., 635 (1966).
47. J. B. Hendrickson, C. Foote, and N. Yoshimura, Chem. Comm., 165 (1965).
48. J. B. Hendrickson, T. L. Bogard, and M. E. Fisch, J. Amer. Chem. Soc., 92, 5538 (1970).
49. R. V. Stevens, L. E. DuPree, Jr., and P. L. Lowenstein, J. Org. Chem., 37, in press; Chem. Comm., 1585 (1970).
50. I. Ninomaya, T. Naito, and T. Kiguchi, Chem. Comm., 1669 (1970).
51. O. L. Chapman and P. G. Cleveland, Chem. Comm., 1064 (1967).
52. O. L. Chapman and G. L. Eian, J. Amer. Chem. Soc., 90, 5329 (1968).
53. T. Kametani, T. Hohno, S. Shibuya, and K. Fukumoto, Chem. Comm., 774 (1971).
54. S. Minami and S. Uyeo, Chem. Pharm. Bull. (Tokyo), 12, 1012 (1964).
55. M. Gates and G. Tschudi, J. Amer. Chem. Soc., 78, 1380 (1956).
56. M. Tomita and S. Minami, Yakugako Zasshi, 33, 1022 (1963).
57. T. Takahashi, M. Yori, and A. Kanbara, Chem. Pharm. Bull (Tokyo), 7, 917 (1959).
58. J. Koizumi, S. Kobayashi, and S. Uyeo, Chem. Pharm. Bull. (Tokyo), 12, 696 (1964).
59. N. Hakama H. Irie, T. Mizutani, T. Shingu, M. Takada, S. Uyeo, and A. Yoshitake, J. Chem. Soc. (C) 2947 (1968).
60. Y. Misaka, T. Mizutani, M. Sekido, and S. Uyeo, J. Chem. Soc. (C), 2954 (1968); Chem. Comm., 1258 (1967).
61. R. K. Hill, J. A. Joule, and L. J. Loeffler, J. Amer. Chem. Soc., 84, 4951 (1962).
62. R. B. Kelly, W. I. Taylor, and K. Wiesner, J. Chem. Soc., 2094 (1953).
63. G. Humber, H. Kondo, K. Kotera, S. Takaga, K. Takeda, W. I. Taylor, B. R. Thomas, Y. Tsuda, K. Tsukamoto, S. Uyeo, H. Yajima, and N. Yanihara, J. Chem. Soc., 4622 (1954).
64. S. Takagi and S. Uyeo, J. Chem. Soc., (1961).
65. H. M. Fates, E. W. Warnhoff, and W. W. Wildman, J. Amer. Chem. Soc., 77, 5885 (1955).
66. N. Ueda, T. Tokuyama, and T. Sakan, Bull. Chem. Soc. (Japan), 39, 2012 (1966).
67. R. G. Naik and T. S. Wheeler, J. Chem. Soc., 1780 (1938).
68. C. B. Clark and A. R. Pinder, J. Chem. Soc., 1967 (1958).
69. J. F. Bunnett and B. F. Hautflord, J. Amer. Chem. Soc., 83, 1691 (1961).
70. J. F. Bunnett and J. A. Skorcz, J. Org. Chem., 27, 3836 (1962).
71. J. F. Bunnett, and T. Kato, R. R. Flyn, and J. A. Skorcz, J. Org. Chem., 28, 1 (1963).
72. K. Takeda, K. Kotera, S. Mizujami, and M. Kobayashi, Chem. Pharm. Bull. (Japan), 8, 483 (1960).
73. K. Kotera, Tetrahedron, 12, 240 (1961).
74. K. Kotera, Tetrahedron, 12, 248 (1961).
75. H. Irie, Y. Nishitani, M. Sugita, and S. Uyeo, Chem. Comm., 1313 (1970).
76. R. T. Arnold and E. C. Coyner, J. Amer. Chem. Soc., 66, 1542 (1944).
77. R. Quelet, R. Duran, and G. Lukacs, Compt. Rend., 258, 1826 (1964).
78. R. Dran and T. Prange, Compt. Rend., 262, 02 (1966).
79. K. Kotera, Tetrahedron, 12, 240 (1961).
80. N. Uneda, T. Tokuyama, and T. Dakan, Bull. Chem. Soc. Japan, 39, 2012 (1966).
81. R. K. Hill and R. M. Carlson, J. Org. Chem., 30, 1571 (1965); Tetrahedron Lett., 1157 (1964).
82. D. H. R. Barton and G. W. Kirby, J. Chem. Soc., 806 (1962); Proc. Chem. Soc., 392 (1960).
83. Ladenburg, Folkers, and Major, J. Amer. Chem. Soc., 58, 1292 (1936).
84. Czapliski, Kostanecki, and Lampe, Berichte, 42, 831 (1909).
85. Späth, Orechoff, and Kuffper, Berichte, 67, 1214 (1934).
86. Surrey, Mooradian, Cutler, Suter, and Buck, J. Amer. Chem. Soc., 71, 2421 (1949).
87. A. R. Battersby and W. I. Taylor, Eds., Oxidative Coupling of Phenols, Dekker, New York, 1967.
88. R. A. Abramovitch and S. Takahashi, Otem. Ind., 1039 (1963).
89. B. Franck and H. J. Lubs, Justus Liebigs Ann. Otem., 720, 131 (1968).
90. B. Franck and H. J. Lubs, Angew. Otem. Int. Ed., 7, 223 (1968).
91. M. Schiebel, Dissertation, Universität Göttingen, 1965.
92. T. Kametani, K. Yamaki, H. Tagi, and K. Fukumoto, J. Chem. Soc. (C), 2602 (1969).
93. D. D. Vaghant and J. R. Merchant, J. Chem. Soc., 1066 (1961).
94. A. H. Jackson and J. A. Martin, J. Chem. Soc. (C), 2061 (1966).
95. M. A. Schwartz and R. A. Holton, J. Amer. Chem. Soc., 92, 1090 (1970); 91, 2800 (1969).
96. B. Franck and H. J. Lubs, Angew. Otem. Int. Ed., 7, 223 (1968).
97. A. Goosen, E. V. O. John, F. L. Warren, and K. C. Yates, J. Chem. Soc., 4028 (1961).
98. W. Rolionow, Butt. Soc. Chim. France, 39, 305 (1926).
99. M. W. Whitlock and G. L. Smith, J. Amer. Chem-Soc., 89, 8600 (1967).
100. D. B. McLean, The Alkaloids, 10, 305 (1968);
101. R. H. F. Manske, The Alkaloids, 5, 295 (1955);
102. K. Wiesner, Fortsch. Otem. Org. Naturstoffe, 20, 271 (1962).
103. K. Wiesner, W. A. Ayer, L. R. Fowler, and Z. Valenta, Otem. Ind., 564 (1957).
104. W. A. Ayer, D. A. Law, and K. Piers, Tetrahedron Lett., 2959 (1964).
105. F. A. L. Anet, Tetrahedron Lett., 13 (1960).
106. W. A. Ayer, D. A. Law, and J. Berezowski, Can. J. Chem., 41, 649 (1963).
107. W. A. Ayer, J. A. Berezowsky, and G. G. Iverach, Tetrahedron, 18, 567 (1962).
108. W. A. Ayer and G. G. Iverach, Can. J. Chem., 38, 1823 (1960)
109. W. A. Harrison, M. Curcumelli-Rodostamo, D. F. Carson, L. R. C. Barclay, and D. B. MacLean, Can. J. Chem., 39, 2086 (1961).
110. F. A. L. Anet and M. V. Rao, Tetrahedron, Lett., 9 (1960).
111. R. H. Burnell and D. R. Taylor, Tetrahedron, 15, 473 (1961).
112. R.H. Burnell and D. R. Taylor, Tetrahedron, 18, 1467 (1962).
113. J. C. F. Yang and D. B. MacLean, Can. J. Chem., 41, 2731 (1963).
114. A. Reissert, Chem. Ber., 24, (1891).
115. W. L. Mosby, in The Chemistry of Heterocyclic Compounds, Vol. 15B (A. Weissberger, Ed.), Interscience, New York.
116. F. G. Mann and B. B. Smith, J. Chem. Soc., 1898 (1951).
117. F. G. Mann and P. I. Ittyerah, J. Chem. Soc., 467 (1958).
118. P. A. S. Smith and T. Yu, J. Amer. Chem. Soc., 74, 1096 (1952).
119. D. B. Glass and A. Weissberger, Org. Synthesis, 26, 40 (1946).
120. R. E. Rindfusz andd V. L. Harnack, J. Amer. Chem. Soc., 42, 1720 (1920).
121. Z. Vanlenta, P. Deslongchamps, R. Ellison, and J. K. Wiesner, J. Amer. Chem. Soc., 86, 2533 (1964).
122. V. Boekeiheide and G. P. Quinn, J. Amer. Chem. Soc., 70, 2830 (1948).
123. M. Protiva and V. Prelog, Helv. Chim. Acta, 32, 621 (1949).
124. N. J. Leonard and M. J. Middleton, J. Amer. Chem. Soc., 74, 5114 (1952).
125. F. Bohlmann and C. Arndt, Chem. Ber., 91, 2167 (1958).
126. F. Bohlmann, Chem. Ber., 91, 2157 (1958).
127. E. Wenkert, N. J. Leonard, L. A. Miller, and P. D. Thomas, J. Amer. Chem. Soc., 78, 3463 (1956) and references cited therein.
128. K. Tsuda and S. Saeki, Chem. Pharm. Bull. (Tokyo), 6, 391 (1958).
129. L. Mandell, J. U. Piper, and K. P. Singh, J. Org. Chem., 28, 3440 (1963);
130. L. Mandell, B. A. Hall, and K. P. Singh, J. Org. Chem., 29, 3067 (1964).
131. E. Wenkert, K. G. Dave, F. Haglid, R. G. Lewis, T. Oishi, R. V. Stevens, and M. Terashima, J. Org. Chem., 33, 747 (1968).
132. E. Wenkert and B. Wickberg, J. Amer. Chem. Soc., 87, 1580 (1965).
133. E. Wenkert, Acct. Chem. Res.
134. E. Wenkert, K. G. Dave, and R. V. Stevens, J. Amer. Chem. Soc., 96, 6177 (1968).
135. E. Wenkert, K. G. Dave, and R. V. Stevens, J. Amer. Chem. Soc., 90, 6177 (1968).
136. E. P. Anderson, J. V. Crawford, and M. L. Sherrill, J. Amer. Chem. Soc., 68, 1294 (1946).
137. E. Colvin, J. Martin, W. Parker, and R. A. Raphael, Chem. Comm., 596 (1966).
138. Z. Horii, S. W. Khim, T. Imanishi, and T. Momose, Chem. Pharm. Bull., 18, 2235 (1970) and references cited therein.
139. A. C. Cope and M. E. Synerholm, J. Amer. Chem. Soc., 72, 5228 (1950).
140. E. Colvin and W. Parker, J. Chem. Soc., 5764 (1965).
141. Z. Valenta, P. Deslongchamps, R. A. Ellison, and K. Wiesner, J. Amer. Chem. Soc., 86, 2533 (1964).
142. G. Pinkus, Chem. Ber., 25, 2798 (1892).
143. N. J. Leonard and J. A. Adanick, J. Amer. Chem. Soc., 81, 595 (1959).
144. H. Dugas, R. A. Ellison, Z. Valenta, K. Wiesner, and C. M. Wong, Tetrahedron Lett., 1279 (1965).
145. E. H. Böhme, Z. Valenta, and K. Wiesner, Tetrahedron Lett., 2441 (1965).
146. I. N. Nazarov and S. I. Zar'valov, Zhur, Obshchei Khim., 24, 469 (1954).
147. K. Wiesner, I. Jirkovský, M. Fishman, and C. A. J. Williams, Tetrhaedron Lett., 1523 (1967).
148. C. A. Grob and H. J. Wilkens, Helv. Chim. Acta, 48, 808 (1965).
149. K. Wiesner and I. Jirkovský, Tetrahedron Lett., 2077 (1967).
150. W. Nigata, S. Hirai, H. Itazaki, and K. Takeda, J. Org. Chem., 26, 2413 (1961).
151. K. Wiesner, Z. Valenta, W. A. Ayer, L. R. Fowler, and J. E. Francis, Tetrahedron, 4, 87 (1958).
152. Z. Valenta, F. W. Stonner, C. Bankiewicz, and K. Wiesner, J. Amer. Chem. Soc., 78, 2867 (1956).
153. D. B. MacLean and H. C. Prime, Can. J. Chem., 31, 543 (1953).
154. H. Dugas, M. E. Hazenberg, Z. Valenta, and K. Wiesner, Tetrahedron Lett., 4931 (1967).
155. H. Reinsliagen, Annalen, 681, 84 (1965).
156. K. Wiesner and L. Poon, Tetrahedron Lett., 4937 (1967); Can J. Chem., 47, 433 (1969).
157. E. E. Betts and D. B. MacLean, Can. J. Chem., 35, 211 (1957).
158. K. Wiesner, V. Musil, and K. J. Wiesner, Tetrahedron Lett., 5643 (1968).
159. G. Stork, R. A. Kretchmer, and R. H. S. Schlessinger, J. Amer. Chem. Soc., 90, 1647 (1968).
160. N. L. Allinger and C. K. Riew, Tetrahedron Lett., 1269 (1966).
161. G. Stork and P. Hudrlik, J. Amer. Chem. Soc., 90, 4462, 4464 (1968).
162. W. A. Ayer, W. R. Bowman, T. C. Joseph, and P. Smith, J. Amer. Chem. Soc., 90, 1648 (1968).
163. W. A. Ayer, W. R. Bowman, G. A. Cooke, and A. C. Soper, Tetrahedron Lett., 2021 (1966).
164. G. F. H. Green and A. G. Long, J. Chem. Soc., 2332 (1961).
165. N. J. Leonard, in The Alkaloids, Vol. I, (R. H. F. Manske and H. L. Holmes, Ed.), Academic, New York, 1950, pp. 108-164.
166. N. J. Leonard, in The Alkaloids, Vol. VI, (R. H. F. Manske and H. L. Holmes, Eds.), Academic, New York, 1960, pp. 37-121.
167. F. L. Warren, in The Alkaloids Vol. XII, (R. H. F. Manske and H. L. Holmes, Eds.), Academic, New York, 1970, pp. 246-331.
168. N. K. Kochetkov and A. M. Likhosherstov, in Advances in Heterocyclic Chemistry Vol. 5 (A. R. Katritzky, Ed.), Academic, New York, 1965, pp. 315-367.
169. F. L. Warren, in Progress in the Chemistry of Organic Natural Products, Vol. XII (E. Zechmeister, Ed.), Springer-Verlan Wien, 1955, pp. 198-269.
170. D. F. L. Warren, in Progress in the Chemistry of Organic Natural Products, Vol. XXIV, (E. Zechmeister, Ed.), Springer-Verlag, Wein, 1966, pp. 329-406.
171. A. S. Labenskii and G. P. Men'shikov, Zh. Obshch. Khim., 18, 1936 (1948); Chem. Abstr., 43, 3827 (1949).
172. R. Adams and K. E. Hamlin, Jr., J. Amer. Chem. Soc., 64, 2597 (1942).
173. N. K. Hart, S. R. Johns, J. A. Lmaberton. Austral. J. Chem., 21, 1393 (1968).
174. G. P. Men'shikov and G. M. Borodina, Zh. Obshch. Khim., 15, 225 (1945); Chem. Abstr., 44, 1484(1950).
175. F. Galinovsky, H. Goldberger, and M. Pöhm, Monatsh. Chem., 80, 550 (1949).
176. A. S. Labenskii, N. A. Serova, and G. P. Men'shikov, Dokl. Akad. Nauk SSSR, 88, 467 (1953); Chem. Abstr., 48, 2721 (1954).
177. A. M. Likhosherstov, V. N. Kulakov, and N. K. Kochetkov, Zh. Obshch. Khim., 34, 2798 (1964); Chem. Abstr., 61, 14734 (1964).
178. F. L. Warren and M. E. von Klemperer, J. Chem. Soc., 4574 (1958).
179. R. A. Konovalova and A. Orekhov, Chem. Ber., 69, 1908 (1936).
180. N. J. Leonard and D. L. Felley, J. Amer. Chem. Soc., 72, 2537 (1950).
181. N. K. Kochetkov, A. M. Likhosherstov, and E. I. Budovskii, Zh. Obshch. Khim., 30, 2077 (1966); Chem. Abstr., 55, 7386i (1961).
182. A. M. Likhosherstov, L. M. Likhosherstov, and N. K. Kochetkov, Zh. Obshch. Khim., 33, 1801 (1963).
183. N. J. Leonard and S. W. Blum, J. Amer. Chem. Soc., 82, 503 (1960).
184. K. Babor, I. Jezo, V. Kalác, and M. Karvas, Chem. Zvesti, 13, 163 (1969); Chem. Abstr., 53, 20107(1959).
185. O. Cervinka, K. Pelz, and I. Jirkovský, Collection Czech. Chem. Comm., 26, 3116 (1961).
186. L. Mandell and W. A. Blanchard, J. Amer. Chem. Soc., 79, 2343, 6198 (1957).
187. N. K. Kochetkov, A. M. Likhosherstov, and A. S. Labedeva, Zh. Obshch. Khim., 31, 3461 (1961); Chem. Abstr., 57, 3490 (1962).
188. M. D. Nair and R. Adams, J. Org. Chem., 26, 3059 (1961);
189. R. Adams, S. Miyano, and M. D. Nair, J. Amer. Chem. Soc., 83, 3323 (1961).
190. N. J. Leonard and T. Sato, J. Org. Chem., 34, 1066 (1969).
191. I. Jezo and V. Kalác, Chem. Zvesti, 11, 696 (1957); Chem. Abstr., 52, 10052 (1958).
192. A. M. Likhosherstov, A. M. Kritsyn, and N. K. Kochetkov, Zh. Obshch. Khim., 32, 2377 (1962); Chem. Abstr., 58, 9154 (1963).
193. K. Babor, J. Jezo, V. Kalac, M. Karvas, and K. Tihlarik, Chem. Zvesti, 14, 679 (1960); Chem. Abstr., 55,17620 (1961).
194. A. J. Aasen and C. C. J. Culvenor, J. Org. Chem., 34, 4143 (1969).
195. T. A. Geissman and A. C. Waiss, Jr., J. Org. Chem., 27, 139 (1962).
196. J. J. Tufariello and J. P. Tette, Chem. Comm., 469 (1971).
197. J. B. Cloke, J. Amer. Chem. Soc., 51, 1174 (1929);
198. see also J. B. Cloke, L. H. Baer, J. M. Robbins, and G. E. Smith, J. Amer. Chem. Soc., 67, 2155 (1945) and references cited therein.
199. P. M. Maginnity with J. B. Cloke, J. Amer. Chem. Soc., 73, 49 (1951).
200. K. Blaha and O. Cervinka, in Advances in Heterocyclic Chemistry, Vol. 6, Academic, New York, 1966, p. 1949.
201. R. V. Stevens and M. C. Ellis, Tetrahedron Lett., 5185 (1967).
202. R. V. Stevens, M. C. Ellis, and M. P. Wentland, J. Amer. Chem. Soc., 90, 5576 (1968).
203. R. Breslow, in Molecular Rearrangments (P. deMayo, Ed.), Interscience, New York, London, 1963, cf. p. 239.
204. H. Gilman and S. M. Spatz, J. Org. Chem., 16, 1485 (1951).
205. C. Dupin and R. Fraisse-Jullien, Bull. Soc. Chim. France, 1993 (1964).
206. F. Bohlmann and O. Schmidt, Chem. Ber., 97, 1354 (1964);
207. M. E. Kuehne and C. Bayha, Tetrahedron Lett., 1311 (1966).
208. E. Wenkert, K. G. Dave, R. G. Lewis, T. Uishi, R. V. Stevens, and M. Terashima, J. Org. Chem., 33, 747 (1968).
209. J. Szmuszkovicz, in Advances in Organic Chemistry, Vol. 4, Interscience, New York, 1963;
210. I. Fleming and M. N. Karger, J. Chem. Soc. (C), 226 (1967).
211. F. C. Tahk and S. L. Keely, Jr., Chem. Comm., 441 (1968).
212. T. J. Curphey and H. L. Kim, Tetrahedron Lett., 1441 (1968).
213. R. V. Stevens and M. P. Wentland, Tetrahedron Lett., 2613 (1968).
214. R. V. Stevens and M. P. Wentland, J. Amer. Chem. Soc., 90, 5580 (1968).
215. R. B. Woodward, Abstracts, 20th National Organic Symposium of the American Chemical Society, Burlington, Vt., June, 1967, p. 104.
216. E. L. Eliel, N. L. Allinger, S. J. Angyal, and G. A. Morrison, Conformational Analysis, Interscience, New York, 1965, p. 314.
217. E. Kaiser and C. Hauser, J. Amer. Chem. Soc., 88, 2348 (1966).
218. R. R. Arndt and P. E. J. Kruger, Tetrahedron Lett., 3237 (1970).
219. R. V. Stevens and L. E. DuPree, Chem. Comm., 1585 (1970);
220. R. V. Stevens, L. E. DuPree, and P. L. Loewstein, J. Org. Chem., in press (1972).
221. For recent reviews on Erythrina alkaloids, see V. Voekelheide, Alkaloids, 7, 201 (1960)
222. R. K. Hill, Alkaloids, 9, 483 (1967).
223. R. V. Stevens and M. P. Wentland, Chem. Comm., 1104 (1968).
224. K. Wiesner, Z. Valenta, A. J. Manson, and F. W. Stonner, J. Amer. Chem. Soc., 77, 675 (1955);
225. see also V. Prelog, A. Langemann, O. Rodig, and M. Ternbah, Helv. Chim. Acta, 42, 1301 (1959).
226. R. V. Stevens, R. K. Mehra, and R. L. Zimmerman, Chem. Comm., 877 (1969).
227. G. Stork and J. E. Dolflni, J. Amer. Chem. Soc., 85, 2872 (1963).
228. Y. Ban, Y. Sato, I. Inove, M. Nagi, T. Oishi, M. Terashima, O. Yonemitsu, and Y. Kanoako, Tetrahedron Lett., 2261 (1965).
229. R. V. Stevens, J. M. Fitzpatrick, M. Kaplan, and R. L. Zimmerman, Chem. Comm., 857 (1971).
230. E. Wenkert, K. G. Dave, and R. V. Stevens, J. Amer. Chem. Soc., 90, 6177 (1968).
231. H. A. Lloyd, E. A. Kielar, R. J. Highet, S. Uyeo, H. M. Fales, and W. C. Wildman, J. Org Chem., 21, 373 (1962)..Contains the synthesis of a degradation product of powellane and several references to interconversions between alkaloids of the series.
232. W. C. Wildman, J. Amer. Chem. Soc., 80, 2567 (1958). The structures of crinine, powelline, buphanidrine, and buphasine proved by degradation and partial synthesis.
233. H. M. Fales and W. C. Wildman, J. Amer. Chem. Soc., 82, 197 (1960).
234. H.-G. Boit and H. Ehmke, Chem. Ber., 89, 2093 (1956). 6-Hydroxycrinamine → criwelline.
235. H. Irie, Y. Tsuda, and S. Uyeo, J. Chem. Soc., 1446 (1959).
236. T. Ikeda, W. I. Taylor, Y. Tsuda, S. Uyeo, and H. Yajima, J. Chem. Soc., 4749 (1956).
237. C. F. Murphy and W. C. Wildman, Tetrahedron Lett., 3863 (1964).
238. W. Döpke, Arch. Pharm., 298, 704 (1965). The conversion of tubispacin into powellane, epoxypowellane, and epiepoxypowellane.
239. S. Uyeo, H. M. Fales, R. J. Highet, and W. C. Wildman, J. Amer. Chem. Soc., 80, 2590 (1958). Haemanthidine -* apohaemanthidine -* dihydroapohaemanthamine ← haemanthamine.
240. H. M. Fales and W. C. Wildman, J. Org. Chem., 26, 181 (1961). Partial synthesis.
241. H. M. Fales and W. C. Wildman, J. Amer. Chem. Soc., 82, 3368 (1960). A summary of the interconversions of alkaloids related to crinine.
242. E. W. Warnhoff and W. C. Wildman, Chem. Ind. (London), 1293 (1958). Undulatine → powellane.
243. H.-G. Boit and W. Döpke, Chem. Ber., 91, 1965 (1958). Crinamine and haemanthamine → haemultine.
244. H.-G. Boit and W. Stender, Chem. Ber., 89, 161 (1956). Haemanthidine → tazettine.
245. W. C. Wildman, Chem. Ind. (London), 123 (1956). Haemanthidine → tazettine.
246. L. Bubewa-lawanoa, Chem. Ber., 95, 1348 (1962). Galanthamine epigalanth-amme-Narwedme.
247. G. P. Volpp and L. Budewa-lwanowa, Chem. Ber., 97, 563 (1964).
248. J. Koizumi, S. Kobayashi, and S. Uyeo, Chem. Pharm. Bull. (Tokyo), 12, 696 (1964).
249. S. Uyeo and S. Kobayashi, Chem. Pharm. Bull. (Tokyo), 1, 139 (1953). Galanthamine → dihydrogalanthamine = lycoramine.
250. H. M. Fales and W. C. Wildman, J. Amer. Chem. Soc., 80, 4395 (1958). The conversion of lycorine → caranine, methyl pseudolycorine → pluviine, powelline → dihydroepicrinine, and buphanidrine → buphanisine is described.
251. L. G. Humber, H. Kondo, K. Kotera, S. Takagi, K. Takeda, W. I. Taylor, B. R. Thomas, Y. Tsuda, K. Tsukamoto, S. Uyeo, H. Yajima, and N. Yanaihara, J. Chem. Soc., 4622 (1954).
252. F. Benington and R. D. Morin, J. Org. Chem., 27, 143 (1962).
253. K. Kotera, Tetrahedron, 12, 240 (1961).
254. K. Kotera, Tetrahedron, 12, 248 (1961)
255. S. Mizukami, Tetrahedron, 11, 89 (1960).
256. R. B. Kelly, W. I. Taylor, and K. Wiesner, J. Chem. Soc., 2094 (1953).
257. W. Döpke, Arch. Pharm., 295, 920 (1962). Partial synthesis of hippamine = 2-O- methylly corine.
258. K. Takeda, K. Kotera, et al., Chem. Pharm. Bull. (Tokyo), 8, 483 (1960).
259. K. Takeda and K. Kotera, Chem. Pharm. Butt. (Tokyo), 5, 234 (1957). Partial synthesis of aulamine = 2-O-acetyl lycorine.
260. H.-G. Boit and H. Ehmke, Chem. Ber., 90, 57 (1957). Oxidation of nerinine to alboma-culine.
261. B. Mehlis, Naturwissenschaften, 52, 33 (1965). Conversion of clivimine to clivonine.
262. T. Kitagawa, S. Uyeo, and N. Yokoyama, J. Chem. Soc., 3741 (1959). Chemically interrelated hydrogenation products of lycorenine, homolycorine, and pluviine.
263. D. F. C. Garbutt, P. W. Jeffs, and F. L. Warren, J. Chem. Soc., 5011 (1962). Krigenamine converted to falcatine methiodide.
264. T. Kitagawa, W. I. Taylor, S. Uyeo, and H. Yajima, J. Chem. Soc., 1066 (1955). Lycorenine → homolycorine.
265. H.-G. Boit, L. Paul, an W. Stender, Chem. Ber., 88, 133 (1955). Lycorenine → homolycorine.
266. S. Uyeo and H. Yajima, J. Chem. Soc., 3393 (1955). Related via their Emde bases.
267. H.-G. Boit and H. Ehmke, Chem. Ber., 90, 57 (1957). Nerinine → albomaculine.
268. R. B. Kelly, W. I. Taylor and K. Wiesner, J. Chem. Soc., 2094 (1953).
269. L. G. Humber, et al., J. Chem. Soc., 4622 (1954). Synthesis of anhydrolycorine methiodide.
270. H. M. Fales, L. D. Giuffrida, and W. C. Wildman, J. Amer. Chem. Soc., 78, 4145 (1956). Narcissamine → galanthamine methiodide.
271. 3H in excess trifluoroacetic anhydride in which it is postulated the 7V-oxidation is suppressed by formation of an acyl-ammonium complex.
272. A. J. Aasen and C. C. J. Culvenor, Austral. J. Chem., 22, 2657 (1969).
273. A. R. Mattocks, J. Otem. Soc. (C), 1155 (1969); see also Ref. 44. Methods are given for the conversion of various dehydTpyrrolizidine alkaloids and their 7V-oxides into dihydropyrrolizine derivatives. The latter substances have been suggested as the toxic metabolites of these alkaloids in animals.
274. C. C. J. Culvenor, J. A. Edgar, L. W. Smith, and H. J. Tweeddale, Tetrahedron Lett., 3599 (1969); see also Ref. 34.
275. A. J. Aasen, C. C. J. Culvenor, and L. W. Smith, J. Org. Chem., 34, 4137 (1969).
276. B. Luning and H. Trankner, Acta Chem. Scand., 22, 2324 (1968). The structure of (+)- l-(methoxycarbonyl)pyrrolizidine was proved by degradation into pyrrolizidine, by reduction to lindelofidine, and by synthesis.
277. L. B. Bull, C. C. J. Culvenor, and A. T. Dick, Frontiers of Biology, Vol. 9, Interscience, New York, 1968.
278. C. C. J. Culvenor, G. M. O'Donovan, and L. W. Smith, Austral. J. Chem., 20, 757 (1967). Two new alkaloids (10,20-epoxy-la-hydroxymethyl-8ot-pyrrolizidine and 7/3- acetoxy-l-methoxymethyl-l, 2-dehydro-8a-pyrrolizidine) were isolated and characterized, and their partial synthesis was executed.
279. R. Schoental, Potential Carcinogenic Hazards Drugs, Proc. Symp., (R. Truhaut, Ed.), 1965, pp. 152-61.
280. O. Cervinka, Chem. Listy., 52, 307 (1958).
281. F. Micheel and W. Flitsch, Chem. Ber., 88, 509 (1955).
282. L. J. Dry, M. J. Koekemoer, and F. L. Warren, J. Chem. Soc., 59 (1955).
283. M. S. Koekemoer and F. L. Warren, J. Chem. Soc., 63 (1955).
284. C. C. J. Culvenor, Austral. J. Chem., 7, 287 (1954). The conversion of supinidine to (-)-isoretronecanol is described.
285. R. Adams and B. L. van Duren, J. Amer. Otem. Soc., 76, 6379 (1954). Conversion of platynecine to anhydroplatynecine.
286. A. D. Kuzovkov and G. P. Men'shikov, Zh. Obshch. Khim., 21, 2245 (1951); Chem. Abstr., 46, 8130a (1952).
287. A. V. Danilova and R. A. Konovalova, Zh. Obshch. Khim., 20, 1921 (1950); Chem. Abstr.. 45, 2960a (1951). Conversion of renardine into renarcine.
288. G. P. Men'shikov and E. L. Gurevich, Zh. Obshch. Khim., 19, 1382 (1949); Chem. Abstr., 44, 3486a (1950). Reduction of supinidine to isoretronecanol.
289. G. P. Men'shikov and A. D. Kuzovkov, Zh. Obshch. Khim., 19, 1702 (1949); Chem. Abstr., 44, 1113g (1950). Chromic acid oxidation of hydroxyheliotridane to retronecanol.
290. N. J. Leonard and D. L. Felley, J. Amer. Chem. Soc., 71, 1758 (1949).
291. N. J. Leonard and G. L. Shoemaker, J. Amer. Chem. Soc., 71, 1760 (1949).
292. N. J. Leonard and G. L. Shoemaker, J. Amer. Chem. Soc., 71, 1762 (1949).
293. N. J. Leonard and K. M. Beck, J. Amer. Chem. Soc., 70, 2504 (1948).
294. N. J. Leonard, L. R. Hruda, and F. W. Long, J. Amer. Chem. Soc., 69, 690 (1947).
295. R. Adams and N. J. Leonard, J. Amer. Chem. Soc., 66, 257 (1944). The synthesis of retronecanone is described.
296. G. Menschikoff, Chem. Ber., 69, 1802 (1936).