Natural aliphatic oxygenated unsaturated acids. Synthesis and biological activity

Russian Chemical Reviews

Volumn 65, Issue 5, 1996, Pages 441-459

  Tolstikov, A G ^a   Tolstikov, G A ^b  

^a BORESKOV INSTITUTE OF CATALYSIS   (Russian Federation)

^b N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2442745711     PISSN: 0036021X     EISSN: None     Source Type: Journal    
DOI: 10.1070/RC1996v065n05ABEH000219     Document Type: Article

References (173)

1. H Baumann, M Bühler, H Fochem, F Hirsinger, J Falbe Angew. Chem. 100 46 (1988)
2. [Angew. Chem., Int. Ed. Engl. 27 42 (1988)]
3. D Bishop J. Lipid Res. 481 (1963)
4. P Ishida, H Shirahama, T Matzumoto Chem. Lett. 9 (1993)
5. C R Smith, T L Wilson, T K Miwa, H Zobel, R Lohmar, J A Wolff J. Org. Chem. 26 2903 (1961)
6. R Biuder, A Lee J. Org. Chem. 31 1477 (1966)
7. H Koshina, S Togija, T Ioshihara, S Sakamura Tetrahedron Lett. 28 73 (1987)
8. D T Asil'bekova, S D Gusakova, A I Glushenkova Khim. Prir. Soedin. 616 (1991)
9. A N Grechkin, O S Korolev, R A Kuramshin, I A Tarchevskii Dokl. Akad. Nauk SSSR 297 1257 (1987)
10. A V Kuchin, A G Tolstikov, E V Gorobets, V N Odinokov, A N Grechkin, G A Tolstikov Dokl. Akad. Nauk SSSR 308 384 (1989)
11. J Joshida, M Nakagama, H Seki, T Hino J. Chem. Soc., Perkin Trans. 1 343 (1992)
12. C Fryhle, P Willard, C Rybak Tetrahedron Lett. 33 2327 (1992)
13. S Tsuboi, Han Wu, S Malda, S Ono, A Kuroda Bull. Chem. Soc. Jpn. 60 1103 (1987)
14. C Smith, T Wilson J. Am. Chem. Soc. 82 1417 (1960)
15. T G Nemyrko, Ya V Rashkes, A I Glushenkova, in Novoe v Biologicheskoi Khimii i Farmakologii Oblepikhi (Advances in the Biochemistry and Pharmacology of Sea Buckthorn (Novosibirsk: Siberian Branch of the Academy of Sciences of the USSR, 1991) p. 85
16. A Verneughi Can. J. Botan. 64 973 (1986)
17. J-M Duffarlt, J Einhorn, A Alexakis Tetrahedron Lett. 32 3701 (1991)
18. C Smith, T Wilson J. Org. Chem. 27 3112 (1962)
19. J Kobayashi, S Okamoto, T Shimazari, J Ochiai, F Sato Tetrahedron Lett. 30 3959 (1987)
20. W Karrer, in Konstitution und Vorkaumen der Organischen Pflauzenstoffe Vol. 2 (Wien: Ergäuzungsbanch, ) p. 1037
21. R Rowell, C Smith J. Org. Chem. 31 528 (1966)
22. C Chan, P Cox, S Roberts J. Chem. Soc., Chem. Commun. 971 (1988)
23. G Moustakis, O Weerasinghe, J Falk Tetrahedron Lett. 27 303 (1986)
24. A Rama Rao, S Reddy, R Reddy J. Org. Chem. 51 4158 (1986)
25. S D Gusakova, D T Esil'bekova Khim. Priv. Soedin. 744 (1991)
26. A Rama Rao, V Varaprasad, E Reddy Synth. Commun. 21 1143 (1991)
27. T Jeffery Tetrahedron Lett. 34 1133 (1993)
28. M Ubukata, K Kimura, K Isono, J McCloskey J. Org. Chem. 57 6392 (1992)
29. J Huguet, M del Carmen Reges Tetrahedron Lett. 31 4279 (1990)
30. T Kato, J Jamaguchi, T Hitano, N Harada Chem. Lett. 409 (1984)
31. A Rama Rao, R Reddy Tetrahedron Lett. 27 2279 (1986)
32. D Shiw, D Jadagiri, J Falk, J Masferrer, M Schwartzman Tetrahedron Lett. 30 3923 (1989)
33. A Guerriero, M D'Ambrosio, F Pietra Helv. Chim. Acta 71 1094 (1988)
34. A Guerriero, M D'Ambrosio, F Pietra, O Ribes J. Nat. Prod. 53 57 (1990)
35. M D'Auria, L Minale, K Riccio Experientia 44 719 (1988)
36. A Guerriero, M D'Ambrosio, F Pietra Helv. Chim. Acta 73 2183 (1990)
37. M Higgs, J Mulheirn Tetrahedron 37 4259 (1981)
38. M Bernart, W Gerwick Tetrahedron Lett. 29 2015 (1988)
39. V Paul, W Fenical Tetrahedron Lett. 21 3327 (1980)
40. F Gunstone J. Chem. Soc. 1611 (1954)
41. R Sawa, N Matsuda, T Uchida, T Jkeda J. Antibiot. 44 396 (1991)
42. S Kadis, A Ciegler, S Ajl, in Microblal Toxins Vol. 7 (New York: Academic Press, 1971) p. 207
43. Y Ueno Trichotecenes - Chemical, Biological, and Toxicological Aspects Vol. 4 (Elsevier, New York, 1983)
44. W Herz, in Fortscbritte Chem. Org. Natur-Stoffe Vol. 47 (New York: Springer, 1953) p. 153
45. M Solem, Z Jiang, W Gerwick Lipids 24 256 (1989)
46. T Kato, J Jamaguchi, T Hirakawa, N Hoshino Agr. Biol. Chem. 55 1349 (1991)
47. T Kato, J Jamaguchi, M Abe, T Uyehara, T Namai, M Kodama, J Shiobara Tetrahedron Lett. 26 2357 (1985)
48. B Cosse-Kobo, P Messet, R Gree Tetrahedron Lett. 30 4235 (1989)
49. A Panossian, G Avetissian, S Batrakov, S Varbanian, E Gabrielian Planta Medica 47 17 (1983)
50. A G Panosyan Bioorg. Khim. 11 126 (1985)
51. A Panossian Prostaglandins 33 363 (1987)
52. G Sharma, S Rao Tetrahedron Lett. 33 2305 (1992)
53. J Cardellina, H Dahetos, F Marneri Phytochemistry 17 2091 (1978)
54. J Jadav, M Chander Tetrahedron Lett. 31 4349 (1990)
55. P Quinton, T Le Gall Tetrahedron Lett. 32 4909 (1991)
56. H Suemune, T Harabe, K Sakai Chem. Pharm. Bull. 36 3632 (1988)
57. P Schener, in Marine Natural Products Vol. 4 (New York: Academic Press, 1981) p. 40
58. P Schener, in Marine Natural Products Vol. 1 (New York: Academic Press, 1978) p. 85
59. A Prand, R Valls, L Piovetti, B Banaigs Tetrahedron Lett. 34 5437 (1993)
60. N Carballerio, V Negrou J. Nat. Prod. 55 333 (1992)
61. E Aganoglu, J Kornbobst, A Abou-Bichara, C Djerassi Tetrahedron Lett. 24 1111 (1983)
62. Ch Mahmood, J Daulatabad, M Mohaddin Phytochemistry 30 2399 (1991)
63. C Smith Lipids 1 268 (1966)
64. L Crombie, D Morgan J. Chem. Soc., Chem. Commun. 558 (1988)
65. A Lopez, W Gerwick Tetrahedron Lett. 29 1505 (1988)
66. A Guerriero, M D'Ambrosio, F Pietra Helv. Chim. Acta 73 2183 (1990)
67. K Gustafson, M Roman, W Fenical J. Am. Chem. Soc. 111 7519 (1989)
68. Z Pang, O Sterner J. Org. Chem. 56 1233 (1991)
69. M Hamburger, S Handa, G Cordell J. Nat. Prod. 50 281 (1987)
70. Jpn. P. 63 159 390; Ref. Zh. Khim. 37 17 O 120P (1989)
71. T Kato, J Jamaguchi, S Ohnuma, M Kodama Chem. Lett. 577 (1986)
72. J Nagao, T Miyasaka, K Seno, E Fujita, D Shibata, E Doi J. Chem. Soc., Perkin Trans. 1 2439 (1984)
73. S Baertschi, A Brash, T Harris J. Am. Chem. Soc. 111 5003 (1989)
74. E Corey, S Wright J. Org. Chem. 55 1670 (1990)
75. E Corey, R Nagata, S Wright Tetrahedron Lett. 28 4917 (1987)
76. C McIntyre, F Scott, T Simpson, L Trimble J. Chem. Soc., Chem. Commun. 501 (1986)
77. A Etemadi, J Gasche Bull. Soc. Chim. Biol. 47 631 (1965)
78. A Etemadi C. R. Hebd. Seances Acad. Sci., Sec. D 263 835 (1966)
79. A Etemadi, E Lederer Bull. Soc. Chem. Fr. 868 (1964)
80. M Nakanishi, T Hase Bull. Chem. Soc. Jpn. 64 3084 (1991)
81. M Nakanishi, T Hase Chem. Lett. 47 (1991)
82. US P. 4 386 227; Ref. Zh. Khim. 9 3 O 33P (1984)
83. L Semmak, A Zerzout, P Valls Phytochemistry 27 2347 (1988)
84. R Näf, A Velluz Tetrahedron Lett. 32 4487 (1991)
85. A Guerriero, M D'Ambrosio, V Guomo, F Pietra Helv. Chim. Acta 7157 (1988)
86. D Traxler, H Fritz, W Richter Helv. Chim. Acta 60 578 (1977)
87. G Rihs, D Traxler Helv. Chim. Acta 64 1533 (1981)
88. F Van Middlesworth, M Ornstead, D Sehmatz, K Bartizal, K A Fromtling, G Bills, K H Nollstadt, S Honeycutt, M M Zweriuk J. Antibiot. 44 45 (1991)
89. H Chiba, R Kanebo, H Agematu, R Okamoto J. Antibiot. 46 356 (1993)
90. F Van Middlesworth, C Dufresne, J Smith, K Wilson Tetrahedron 47 7563 (1991)
91. L Crombie, M Horsham, S Jarrett Tetrahedron Lett. 30 4299 (1989)
92. S Nakatsuka, K Ueda, T Goto, M Jamamoto, S Nishimura, K Kohmoto Tetrahedron Lett. 27 2753 (1986)
93. T Kitagawa, M Miyashita, Zhang Jang Chem. Pharm. Bull. 39 2445 (1991)
94. H Jrie, K Matsumoto, T Kitagawa Chem. Pharm. Bull. 38 1451 (1990)
95. US P. 5 182 298; Ref. Zh. Khim. 36 9 O 139P (1994)
96. M Adamczeski, E Quinoa, P Crews J. Org. Chem. 55 240 (1990)
97. M Adamczeski, E Quinoa, P Crews J. Am. Chem. Soc. 111 647 (1989)
98. N Chida, T Tobe, Sh Okada J. Chem. Soc., Chem. Commun. 1064 (1992)
99. J Marshall, G Luke J. Org. Chem. 58 6229 (1993)
100. R Jansen, G Reifenstane, K Gerth, H Reichenbach, G Holfe Liebigs Ann. Chem. 1081 (1983)
101. W Trowitsch-Kinnst, E Forsche, H Reichenbach, V Wray Liebigs Ann. Chem. 659 (1992)
102. J Kim, F Furinata, Sh Jamanaka J. Antibiot. 44 553 (1991)
103. BRD P. 4 041 686; Ref. Zh. Khim. 4 7 O 28P (1993)
104. BRD P. 4 041 688; Ref. Zh. Khim. 38 10 O 144P (1993)
105. A Wright, J Coll, J Price J. Nat. Prod. 53 845 (1990)
106. Sh Ohta, H Okada, H Kobayashi, J Oclarit, S Ikegami Tetrahedron Lett. 33 5935 (1993)
107. Jpn. P. 58-150 595; Ref. Zh. Khim. 30 23 O 216P (1994)
108. A Gangloff, B Akemark, P Hequist J. Org. Chem. 57 4797 (1992)
109. T Watanabe, T Suzuki, K Uzaki J. Antibiot. 44 1457 (1991)
110. L Banfi, W Carbi, G Poli, D Potenza, C Scolastico J. Org. Chem. 52 5452 (1987)
111. M Devys, J-P Ferezoy, R Topgi, M Barbier, J -E Bousqret, A Kollman J. Chem. Soc., Perkin Trans. 1 2133 (1984)
112. D O'Hagan, S Rogers, G Diffiu, R Edwards Tetrahedron Lett. 33 5585 (1993)
113. H Seto, T Sasaki, H Jonehara Tetrahedron Lett. 28 4083 (1977)
114. D Aldridge, D Giles, W Turner J. Chem. Soc., C 3888 (1971)
115. S Chatterjee, E Vijayakumar, K Roy, R Rupp, B Ganguli J. Org. Chem. 53 4883 (1988)
116. G Bill, R Chen, R Rasmussen, J McAlpine J. Antibiot. 46 39 (1993)
117. B Jarvis, S N Cömezöglu, M Rao, B Pena, F E Boettner, T M Williams, G Forsyth, B Epling J. Org. Chem. 52 45 (1987)
118. B Jarvis, S Comezogu, H Anmon, S Kupchan J. Nat. Prod. 50 815 (1987)
119. S Yu Yunusov, Alkaloidy (Alkaloids) (Tashkent: FAN, 1981) p. 354
120. A Mattocks Chemistry and Toxicology of Pyrrolizidine Alkaloids (London: Academic Press, 1986)
121. J Harris, J Turner, M Meinz, M Nallin-Omstead, G Helms, G Bills, D Zink, K Wilson Tetrahedron Lett. 34 5235 (1993)
122. C Spino, L Weiler Tetrahedron Lett. 28 731 (1987)
123. C Pace-Asciac, L Wolfe J. Chem. Soc., Chem. Commun. 1235 (1980)
124. G Just, D Crosilla Can. J. Chem. 58 2349 (1980)
125. E Chain, G Mellows J. Chem. Soc., Perkin Trans. 1 294 (1977)
126. G Keck, A Tafesh J. Org. Chem. 54 5845 (1989)
127. D Stierle, A Stierle Experientia 48 1165 (1992)
128. M Balestra, M Wittman, J Kallmerben Tetrahedron Lett. 29 6905 (1988)
129. S Danishefsky, C Selnick, M DeNinno, R Zelle J. Am. Chem. Soc. 109 1572 (1987)
130. B Isaak, S Ager, R Elliot, R Stonard J. Org. Chem. 57 7220 (1992)
131. C Pace-Asciac Biochemistry 10 3664 (1971)
132. A G Tolstikov, O F Prokopenko, L V Spirikhin, G A Tolstikov Bioorg. Khim. 19 262 (1993)
133. G Just, P Povin Can. J. Chem. 58 2173 (1980)
134. G Hofle, H Steinmetz, K Gerth, H Reichenbach Liebigs Ann. Chem. 941 (1991)
135. S Tsukamoto, M Ishibashi, T Sasaki, J Kobayashi J. Chem. Soc., Perkin Trans. 1 3185 (1991)
136. M Yofsu-Yamashita, R Haddock, T Yasumoto J. Am. Chem. Soc. 115 1147 (1993)
137. H Inouye, Y Takaeda, S Uesato, K Uobe, T Hashimoto Tetrahedron Lett. 21 1059 (1980)
138. A Kempf, K Wilson, O Hensens, R Monahan J. Antibiot. 39 1361 (1986)
139. E Selva, G Beretta, R Pallanza J. Antibiot. 43 1349 (1990)
140. J Grove Nat. Prod. Rep. 10 429 (1993)
141. H Koshino, H Takahashi, H Osaka, K Isono J. Antibiot. 45 1420 (1992)
142. B Potts, D Faulkner J. Am. Chem. Soc. 113 6321 (1991)
143. O Hensens, C Dufresne, J Liesch, D Zink, R Reamer, F VanMiddlesworth Tetrahedron Lett. 34 349 (1993)
144. M Dawson, J Farthing, P Marshall, M O'Neil, R Tait, H Wildman, M Hages J. Antibiot. 45 639 (1992)
145. P Sidebothom, R Hitchcock, S Lane, N Watson J. Antibiot. 45 648 (1992)
146. S Grundy New England J. Med. 319 24 (1988)
147. A Baxter, B Fitzgerald, M Sapra, C Wright J. Biol. Chem. 267 11705 (1992)
148. M Lester, G Giblin, G Inglish, P Procopin, B Ross, N Watson Tetrahedron Lett. 34 4357 (1993)
149. A Robichand, G Berger, D Evans Tetrahedron Lett. 34 8403 (1993)
150. Chuen Chan, G Guglis, P Procopin, B Ross, N Watson, A Srikantha Tetrahedron Lett. 34 6143 (1993)
151. C Dufresne, K Wilson, S Singh, D Zink J. Nat. Prod. 56 1923 (1993)
152. E B Gorobets, A V Kuchin, G A Tolstikov Metaloorg. Khim. 4 198 (1991)
153. A Rama Rao, E Reddy, A Purandare Tetrahedron 43 4385 (1987)
154. U Balerao, L Dasaradhi, C Muralikrishna, N Fadnavis Tetrahedron Lett. 34 2359 (1993)
155. J Kobayashi, S Okamoto, F Sato Tetrahedron Lett. 28 3959 (1987)
156. T Jeffrey Tetrahedron Lett. 34 1133 (1993)
157. J M Duffault, J Einhorn, A Alexakis Tetrahedron Lett. 32 3701 (1991)
158. A Rama Rao, E Reddy, J Jadav Tetrahedron 42 4523 (1986)
159. M Gurjar, E Reddy Tetrahedron Lett. 31 1783 (1990)
160. J Jadav, P Radhakrishna Tetrahedron 46 5825 (1990)
161. Ch Moustakis, D Weerasinghe, J Falk Tetrahedron Lett. 27 303 (1986)
162. J Jadav, M Chander Tetrahedron Lett. 31 4349 (1990)
163. Wen-Lian Wu, Ju-Lin Wu Tetrahedron Lett. 33 3887 (1992)
164. E Corey, S Wright J. Org. Chem. 55 1670 (1990)
165. E Corey, A Tramontano J. Am. Chem. Soc. 106 462 (1984)
166. F Naso J. Org. Chem. 56 6245 (1991)
167. Y Guindon, C Yoakim, V Gorys, W W Ogilvie, D Delorme, J Renaud, G Robinson, J-F Lavallée, A Slassi, G Jung, J Rancourt, K Durkin, D Liotta J. Org. Chem. 59 1166 (1994)
168. K Nicolaou, E Jue, J Naniwa, Zhen Jang Angew. Chem., Int. Ed. Engl. 33/21 2184 (1994)
169. K Nicolaou, A Nadin, J Lereche, E Jue Angew. Chem., Int. Ed. Engl. 33/21 2190 (1994)
170. R Johnson, K Sharpless, in Catalytic Asymmetric Synthesis (Ed. A Ojima) (New York: VCH, 1993) p. 227
171. D Dess, J Martin J. Org. Chem. 48 4156 (1983)
172. G A Tolstikov, M S Miftakov, M E Adler Zh. Org. Khim. 24 224 (1988)
173. S Danishetsky, H Selnick, M De Ninno, R Zelle J. Am. Chem. Soc. 109 1572 (1987)