Biocatalysis applied to the synthesis of pheromones

Current Organic Chemistry

Volumn 11, Issue 8, 2007, Pages 693-705

  Aleu, J ^a   Bustillo, A J ^a   Hernandez Galan R ^a   Collado, Isidro Gonzalez ^a  

^a UNIVERSITY OF CÁDIZ   (Spain)

Author keywords

(S) quadrilure; Chemoenzymatic synthesis; Japonilure; Pheromone acetoxy derivatives; Spiroketal pheromones

Indexed keywords

AGRICULTURAL CHEMICALS; HORMONES; STEREOCHEMISTRY;

(S)-QUADRILURE; BIOCATALYSIS; CHEMO-ENZYMATIC SYNTHESIS; ENANTIOPURE; JAPONILURE; PHEROMONE ACETOXY DERIVATIVE; REGIOSELECTIVE FUNCTIONALIZATION; SPIROKETAL PHEROMONE; SPIROKETALS; ]+ CATALYST;

CATALYSTS;

1 3 DIMETHYL 2 9 DIOXABICYCLO[3.3.1] NONANE; 1 3 DIMETHYL 2 9 DIOXOLANE; 1 7 DIOXASPIRO[5.5] UNDECANE; 2 8 DIMETHYL 1 7 DIOXASPIRO[5.5] UNDECANE; 2 METHYL 1 7 DIOXASPIRO[5.5] UNDECANE; 4 HYDROXY 1 7 DIOXASPIRO[5.5] UNDECANE; 5 PHENYL THIOPENTAN 2 OL; 6 ACETOXYHEXADECAN 5 OLIDE; 7 8 EPOXY 2 METHYLOCTADECANE; 7 METHYL 1 6 DIOXASPIRO[4.5] DECANE; BREVICOMIN; DOMINICALUR 1; DOMINICALUR 11; ELDANOLIDE; FARANAL; FRONTALIN; HEXAN 4 OLIDE; ISOBREVICOMIN; JAPONILURE; LEUCOMALURE; MULTISTRIATIN; OCTADEC 9 EN 4 OLIDE; PHEROMONE; PHEROMONE DERIVATIVE; PITYOL; QUADRILURE; SULCATOL; TETRADEC 5 EN 13 OLIDE; TRIBOLURE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

BIOCATALYST; BIOLOGICAL ACTIVITY; BIOTRANSFORMATION; ENANTIOMER; ENZYME ACTIVITY; HORMONE SYNTHESIS; NONHUMAN; REVIEW; STEREOSPECIFICITY;

EID: 34248547349     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527207780598738     Document Type: Review

References (210)

1. Loughlin, W.A. Bioresour. Technol., 2000, 74, 49.
2. b) Koeller, K.M.; Wong, Ch-H. Nature, 2001, 409, 232.
3. Kurihara, N.; Miyamoto, J. Chirality in Agrochemicals, John Wiley & sons: Chichester, U.K., 1998.
4. Shea, P.J. ACS Symp. Ser., (2nd Ed.), 595, 1995.
5. a) Fukusaki, E.; Satoda, S. J. Mol. Cat. B: Enz., 1997, 2, 257.
6. b) Mori, K. Synlett, 1995, 11, 1097.
7. c) Roberts, S.M.; Williamson, N.M. Curr. Org. Chem., 1997, 1, 1.
8. Roberts, S.M. Pure Appl. Chem., 1992, 64, 1153.
9. Davis, H.G.; Green, R.H. Nat. Prod. Rep., 1986, 3, 87.
10. a) Perkins, M.V.; Kitching, W.; Konig, W.A.; Drew, R.A.I. J. Chem. Soc. Perkin Trans. 1, 1990, 2501.
11. b) Perkins, M.V.; Kitching, W.; Drew, R.A.I.; Moore, C.J.; Konig, W.A. J. Chem. Soc. Perkin Trans. 1, 1990, 1111.
12. c) Chen, J.; Fletcher, M.; Kitching, W. Tetrahedron Asymmetry, 1995, 6, 967.
13. Bergstrom, G.; Tengo, J.; Reith, W.; Francke, W. Z. Naturforsch, 1982, 37c, 1124.
14. b) Redlich, H.; Schneider, B. Liebigs Ann. Chem., 1983, 412.
15. Nakamura, K.; Kitayama, T.; Inoue, Y.; Ohno, A. Tetrahedron, 1990, 46, 7471.
16. b) Mori, K.; Katsurada, M. Liebigs Ann. Chem., 1984, 157.
17. c) Francke, W.; Reith, W.; Bergstrom, G.; Tengo, J. Z. Naturforsch, 1981, 36c, 928.
18. Kitayama, T. Tetrahedron, 1996, 52, 6139.
19. Liu, H.; Cohen, T. J. Org. Chem., 1995, 60, 2022.
20. Cohen, T.; Tong, S. Tetrahedron, 1997, 53, 9487.
21. a) Izquierdo, I.; Plaza, M.T.; Rodriguez, M.; Tamayo, J.A.; Martos, A. Tetrahedron Asymmetry, 2001, 12, 293.
22. b) Izquierdo, I.; Plaza, M.T.; Rodriguez, M.; Tamayo, J.A. Tetrahedron Asymmetry, 2000, 11, 1749.
23. Yokohama, Y.; Takikawa, H.; Mori, K. Bioorg. Med. Chem., 1996, 4, 409.
24. Haniotakis, G.; Francke, W.; Mori, K.; Redlich, H.; Schurig, V. J. Chem. Ecol., 1986, 12, 1559.
25. Hu, S.; Jayaraman, S.; Oehlschlager, A.C. J. Org. Chem., 1999, 64, 2524.
26. Oehlschlager, A.C.; Johnston, B.D. J. Org. Chem., 1987, 52, 940.
27. Francke, W.; Schröder, W. Curr. Org. Chem., 1999, 3, 407, and refs. cited therein.
28. Wood, D.L.; Browne, L.E.; Ewing, B.; Lindahl, K.; Bedard, W.D.; Tilden, P.E.; Mori, K.; Pitman, G.B.; Hughes, P.R. Science, 1976, 192, 896.
29. Mayer, S.F.; Mang, H.; Steinreiber, A.; Saf, R.; Faber, K. Can. J. Chem., 2002, 80, 362.
30. a) Myles, D.C.; Andrulis, P.J.; Whitesides, G.M. Tetrahedron Lett., 1991, 32, 4835.
31. b) Sprenger, G.A.; Pohl, M. J. Mol. Cat. B: Enz., 1999, 6, 145.
32. Bel-Rhlid, R.; Renard, M.F.; Veschambre, H. Bulletin de la Societé Chimique de France, 1996, 133, 1011.
33. Ishiyama, J.; Toi, M.; Ichikawa, Ch.; Ot, S.; Inoue, Y. Nippon Kagaku Kaishi, 1993, 10, 1162.
34. Mori, K.; Kiyota, H. Liebigs Ann., 1992, 9, 989.
35. Mori, K.; Takikawa, H.; Nishimura, Y.; Horikiri, H. Liebigs Ann., 1997, 2, 327.
36. Francke, W.; Schrder, F.; Philipp, P.; Meyer, H.; Sinnwell, V.; Gries, G. Bioorg. Med. Chem., 1996, 4, 363.
37. Pearce, G.T.; Gore, W.E.; Silverstein, R.M.; Peacock, J.W.; Cuthbert, P.A.; Lanier, G.N.; Simeone, J.B. J. Chem. Ecol., 1975, 1, 115.
38. a) Sinha, S.C.; Keinan, E. J. Am. Chem. Soc., 1995, 117, 3653.
39. b) Sinha, S.C.; Keinan, E. Isr. J. Chem., 1996, 36, 185.
40. c) Keinan, E.; Sinha, S.C.; Shabat, D.; Itzhaky, H.; Reymond, J.L. Acta Chem. Scand., 1996, 50, 679.
41. Kinzer, G.W.; Fentiman, A.F.; Page, T.F.; Foltz, R.L.; Vité, J.P.; Pitman, G.B. Nature, 1969, 221, 447.
42. Payne, T.L.; Richerson, J.V.; Dickens, J.C.; West, J.R.; Mori, K.; Brisford, C.W.; Hedden, R.L.; Vité, J.P.; Blum, M.S. J. Chem. Ecol., 1982, 8, 873.
43. List, B.; Shabat, D.; Guofu, Z̧ Turner, J.M.; Li, A.; Bui, T.; Anderson, J.; Lerner, R.A.; Barbas III, C.F. J. Am. Chem. Soc., 1999, 121, 7283.
44. Kroutil, W.; Osprian, I.; Mischitz, M.; Faber, K. Synthesis, 1997, 2, 156.
45. Nishimura, Y.; Mori, K. Eur. J. Org. Chem., 1998, 233.
46. Ohta, H.; Kimura, Y.; Sugano, Y.; Sugai, T. Tetrahedron, 1989, 45, 5469.
47. Chênevert, R.; Caron, D., Tetrahedron Asymmetry, 2002, 13, 339.
48. Sugai, T.; Ohta, H.; Kakeya, H. J. Org. Chem., 1990, 55, 4643.
49. Fang, J-M.; Chen, S-T. J. Org. Chem., 1997, 62, 4349.
50. Ferraboschi, P.; Casati, S.; Grisenti, P.; Santaniello, E. Tetrahedron Asymmetry, 1993, 4, 9.
51. Seu, Y.B.; Kho, Y.H. Nat. Prod. Lett., 1994, 4, 61.
52. Dauphin, G.; Fauve, A.; Veschambre, H. J. Org. Chem., 1989, 54, 2238.
53. Mori, K. Chem. Commun., 1997, 1153.
54. Belan, A.; Bolte, J.; Fauve, A.; Gourcy, J.G.; Veschambre, H. J. Org. Chem., 1987, 52, 256.
55. Tidswell, E.C.; Salter, G.J.; Kell, D.B.; Morris, J.G. Enzyme Microb. Technol., 1997, 21, 143.
56. Wu, M-H.; Li, Y.; Chen, ZX.; Yang, G-Ch.; Shi, C-Y. Yingyong Huaxue, 2000, 17, 224.
57. Sugai, T.; Ohta, H. Agric. Biol. Chem., 1990, 54, 1577.
58. Sugai, T.; Katoh, O.; Ohta, H. Tetrahedron, 1995, 51, 11987.
59. Patil, P.N.; Chattopadhyay, A.; Udupa, S. R.; Banerji, A. Biotech. Lett., 1993, 15, 367.
60. Schwab, E.; Bernreuther, A.; Puapoomchareon, P.; Mori, K.; Schreier, P. Tetrahedron Asymmetry, 1991, 2, 471.
61. Da Silva, F.M.; Bastos, F.M.; Oestreicher, E.G.; Pinto, G.F.; Jones Jr, J.; Paiva, L.M.C. Biotech. Tech., 1997, 11, 739.
62. Stampfer, W.; Kosjek, B.; Moitzi, Ch.; Kroutil, W.; Faber, K. Angew. Chem. Int. Ed., 2002, 41, 1014.
63. Mori, K. Tetrahedron, 1981, 37, 1341.
64. Sarma, B.; Barua, N.C. Indian J. Chem., 1993, 32B, 615.
65. Li, Y.; Chen, ZX.; Shi, Ch-Y. Youji Huaxue, 2000, 20, 388.
66. Stokes, T.M.; Oehlschlager, A.C. Tetrahedron Lett., 1987, 28, 2091.
67. Fukunaga, K.; Minamijima, N.; Sugimura, Y.; Kang, Z, Nakao, K. J. Biotech., 1996, 52, 81.
68. Naoshima, Y.; Kamezawa, M.; Tachibana, H.; Munakata, Y.; Fujita, T.; Kihara, K.; Raku, T. J. Chem. Soc. Perkin Trans., 1993, 1, 557.
69. Liang,S.; Paqette, L.A. Tetrahedron Asymmetry, 1990, 1, 445.
70. a) Kita, Y.; Takebe, Y.; Murata, K.; Naka, T.; Akai, S. J. Org. Chem., 2000, 65, 83.
71. b) Kita, Y.; Takebe, Y.; Murata, K.; Naka, T.; Akai, S. Tetrahedron Lett., 1996, 37, 7369.
72. Steinreiber, A.; Stadler, A.; Mayer, S.F.; Faber, K.; Kappe, O. Tetrahedron Lett., 2001, 42, 6283.
73. a) Kruse, W.; Kragl, U.; Wandrey, C. Forschungszentrum Jülich GmbH, Germany, DE 4436149 A1, CAN 124:315156, 1996.
74. b) Liese, A.; Seelbach, K.; Wandrey, C. Industrial Biotransformations, Wiley-VCH, Weinheim, Germany, 2000.
75. Steinreiber, A.; Edegger, K.; Mayer, S.F.; Faber, K. Tetrahedron Asymmetry, 2001, 12, 2067.
76. Archelas, A; Furstoss, R. Tetrahedron Lett., 1992, 33, 5241.
77. Vasilev, A.A.; Vielhauer, O.; Engman, L.; Pietzsch, M.; Serebryakov, E.P. Russian Chem. Bull., Int. Ed., 2002, 51, 481.
78. Zada, A.; Harel, M. Tetrahedron Asymmetry, 2004, 15, 2339.
79. Mori, K.; Ishigami K. Liebigs Ann. Chem., 1992, 1195.
80. Nagaki, M.; Takaya, A.; Maki, Y.; Ishibashi, J.; Kato, Y.; Nishino, T.; Koyama, T. J. Mol. Cat. B: Enz., 2000, 10, 517.
81. Nagaki, M. 2002, Jpn. Pat. JP 2002191390 A2, CAN 137:62273.
82. Zada, A.; Ben-Yehuda, S.; Dunkelblum, E.; Harel, M.; Assael, F.; Mendel, Z J. Chem. Ecol., 2004, 30, 631.
83. Mori, K.; Iwasawa, H. Tetrahedron, 1980, 36, 2209.
84. Domínguez, E.; Carretero, J.C.; Fernández-Mayoralas, A.; Conde, S. Tetrahedron Lett., 1991, 32, 5159.
85. Kamezawa, M.; Raku, T.; Tachibana, H.; Ohtani, T.; Naoshima, Y. Biosci. Biotechnol. Biochem., 1994, 58, 598.
86. Kang, S-K.; Jeon, J-H.; Yamaguchi, T.; Kim, J-S.; Ko, B-S. Tetrahedron Asymmetry, 1995, 6, 2139.
87. Itoh, T.; Mitsukura, K.; Kanphai, W.; Takagi, Y.; Kihara, H.; Tsukube, H. J. Org. Chem., 1997, 62, 9165.
88. Cammaerts, M-C.; Mori, K. Physiol. Entomol., 1987, 12, 381.
89. Mori, K.; Murata, N. Liebigs Ann. Chem., 1995, 697.
90. Ichikawa, A. Chirality, 1999, 11, 338.
91. Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem., 1994, 59, 7201.
92. Sharma, A.; Pawar, A.S.; Chattopadhyay, S. Synth. Commun., 1996, 26, 19.
93. Sharma, A.; Chattopadhyay, S. Tetrahedron Asymmetry, 1997, 8, 4021.
94. Sonnet, Ph.E.; Baillargeon, M.W. J. Chem. Ecol., 1987, 13, 1279.
95. Sonnet, Ph.E. ACS Symp. Series, 1988, 362, 230.
96. Keinan, E.; Sinha, S.C.; Sinha-Bagchi, A. J. Org. Chem., 1992, 57, 3631.
97. Wagner, M.R.; Raffa, K.F. In Sawfly Life History Adaptations to Woody Plants, Academic Press, San Diego, 1993.
98. Larsson, M.; Nguyen, B-V.; Högberg, H-E.; Hedenström, E. Eur. J. Org. Chem., 2001, 353.
99. Lundh, M.; Smitt, O.; Hedenström E. Tetrahedron Asymmetry, 1996, 7, 3277.
100. Nakamura, Y.; Mori, K. Eur. J. Org. Chem., 1999, 2175.
101. Hedenström, E.; Edlund, H.; Lund, S.; Abersten, M.; Persson, D. J. Chem. Soc. Perkin Trans. 1, 2002, 1810.
102. Larsson, M.; Andersson, J.; Liu, R.; Högberg, H-E. Tetrahedron Asymmetry, 2004, 15, 2907.
103. Högberg, H-E.; Berglund, P.; Edlund, H.; Faegerhag, J.; Hedenstrtöm, E.; Lundh, M.; Nordin, O.; Servi, S.; Voerde, C. Catal. Today, 1994, 22, 591.
104. Larcheveqe, M.; Sanner, C.; Azerad, R.; Buission, D. Tetrahedron, 1989, 44, 6407.
105. Naoshima, Y.; Munakata, Y.; Yoshida, S.; Funai, A. J. Chem. Soc. Perkin Trans. 1, 1991, 549.
106. Gläzer, B.I.; Köigsberger, K.; Berger, B.; Faber, K.; Griengl, H. Chem. Phys. Lipids, 1990, 54, 43.
107. Furukawa, A.; Shibata, Ch.; Mori, K. Biosci. Biotechnol. Biochem., 2002, 66, 1164.
108. Mori, K.; Ohtaki, T.; Ohrui, H.; Berkebile, D.R.; Carlson, D.A. Biosci. Biotechnol. Biochem., 2004, 68, 1768.
109. Pawar, A.S.; Chattopadhyay, S. Tetrahedron Asymmetry, 1995, 6, 463.
110. Geresh, Sh.; Valiyaveettil, T.J.; Lavie, Y.; Shani, A. Tetrahedron Asymmetry, 1998, 9, 89.
111. Kamezawa, M.; Tachibana, H.; Ohtani, T.; Naoshima, Y. Biosci. Biotechnol, Biochem., 1993, 57, 1962.
112. Kamezawa, M.; Tachibana, H.; Ohtani, T.; Naoshima, Y. J. Chem. Ecol., 1994, 20, 1057.
113. Chin, Sh-Z, Li, Y.; Chen, ZX. Yingyong Huaxue, 2002, 19, 85.
114. Gamalevich, G.D.; Serebryakov, E.P. Mendeleev Commun., 1994, 40.
115. Gamalevich, G.D.; Morozov, B.N.; Serebryakov, E.P. Izv. Akad. Nauk. Khim., 1996, 204.
116. Vogel, M.; Kordel, A.; Schulze, A. Proceedings of ECSOC-3 and Proceedings of ECSOC-4, 2000, 1443.
117. Kharisov, R.Y.; Petuchova, N.I.; Phaifer, L.V.; Davletova, A.R.; Zarin, V.V.; Ishmuratov, G.Y.; Tolstikov, G.A. Bashkirskii Khimicheskii Zhurnal, 2000, 7, 46.
118. Morgan, B.; Oehlschlager, A.C.; Stokes, T.M. J. Org. Chem., 1992, 57, 3231.
119. Orrenius, C.; Noria, T.; Hule, K.; Carrea, G. Tetrahedron Asymmetry, 1995, 6, 3023.
120. Iwaki, S.; Maruo, S.; Saito, T.; Yamada, M.; Katagiri, K. J. Am. Chem. Soc., 1974, 96, 7842.
121. Bianchi, D.; Cabri, W.; Cesti, P.; Flancalanci, F.; Rama. F. Tetrahedron Lett., 1988, 29, 2455.
122. Otto, P.P.J.H.L.; Stein, F.; Van der Willigen, C.A. Agr. Ecosyst. Environ., 1988, 21, 121.
123. Brevet, J.L.; Mori, K. Synthesis, 1992, 1007.
124. a) Fukusaki, E.; Senda, S.; Nakazono, Y.; Yuasa, H.; Omata, T. J. Ferment. Bioeng., 1992, 73, 280.
125. b) Fukusaki, E.; Senda, S.; Nakazono, Y.; Yuasa, H.; Omata, T. J. Ferment. Bioeng., 1992, 73, 284.
126. Yuasa, H. 1994, Jpn. Pat JP 06022778 A2, CAN 121:7458.
127. Tsuboi, S.; Yamafuji, N.; Utaka, M. Tetrahedron Asymmetry, 1997, 8, 375.
128. Muto, S.; Mori, K. Eur. J. Org. Chem., 2003, 1300.
129. Tumlinson, J.H.; Kleinn, M.G.; Doolittle, R.; Ladd, T.T.; Proveaux, A.T. Science, 1977, 197, 789.
130. Sugai, T.; Ohsawa, S.; Yamada, H.; Ohta, T. Synthesis, 1990, 1112.
131. Fukusaki, E.; Senda, S.; Nakazono, Y.; Omata, T. Tetrahedron, 1991, 47, 6223.
132. Yamada, Y.; Fukusaki, E. Kagaku to Seibutsu, 1993, 31, 531.
133. Taylor, S.K.; Atkinson, R.F.; Almli, E.P.; Carr, M.D.; Van Huis, T.J.; Whittaker, M.R. Tetrahedron Asymmetry, 1995, 6, 157.
134. Matsumura, Y.; Fukawa, H.; Chiba, M.; Endo, T. 2000, Jpn. Pat. JP 2000139493 A2, CAN 132:333456.
135. Satoda, S.; Senda, S.; Komata, T.; Fukusaki, E. 1997, Jpn. Pat. JP 09028393 A2, CAN 126:224352.
136. Fukusaki, E.; Senda, S.; Yuasa, H.; Tanaka, H.; Komata, T. 1994, Jpn. Pat. JP 06217792 A2, CAN 121:279069.
137. Fukusaki, E.; Senda, S.; Nakazono, Y.; Omata, T.; Hibino, K.; Ota, H.; Sugai, T. 1991, Eur. Pat. Appl. EP 435293 A2, CAN 115:278160.
138. Tsuboi, S.; Sakamoto, J.; Uko, M.; Imai, Y. 1990, Jpn. Pat. JP 02291286 A2, CAN 115:27723.
139. Sugai, T.; Mori, K. Agric. Biol. Chem., 1984, 48, 2497.
140. Nakayama, T.; Mori, K. Liebigs Ann., 1997, 839.
141. Taylor, S.K.; Arnold, C.R.; Gerds, A.T.; Ide, N.D.; Law, K.M.; Kling, D.L.; Pridgeon, M.G.; Simons, L.J.; Vyvyan, J.R.; Yamaoka, J.S.; Liao, M-K.; Goyne, T.E. Tetrahedron Asymmetry, 2004, 15, 3819.
142. Naoshima, Y.; Nishiyama, T.; Nakamura, A. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 1988, 30, 111.
143. Naoshima, Y.; Ozawa, H.; Kondo, H.; Hayashi, S. Agric. Biol. Chem., 1983, 47, 1431.
144. Leal, W.S. Naturwissenschaften, 1991, 78, 521.
145. Fukusaki, E.; Senda, S.; Nakazono, Y.; Omata, T. Biosci. Biotech. Biochem., 1992, 56, 1160.
146. Fukusaki, E.; Satoda, S.; Senda, S.; Omata, T. J. Ferment. Bioeng., 1998, 86, 508.
147. Yarger, R.G.; Silverstein, R.M.; Burkholder, W.E. J. Chem. Ecol., 1975, 1, 323.
148. Ravid, U.; Silverstein, R.M.; Smith, L.R. Tetrahedron, 1978, 34, 1449.
149. Mori, K.; Mori, H.; Sugai, T. Tetrahedron, 1985, 41, 919.
150. Ghosh, S.K.; Chattopadhyay, S.; Mamdapur, V.R. Tetrahedron, 1991, 47, 3089.
151. Jacobs, H.K.; Mueller, B.H.; Gopalan, A.S. Tetrahedron, 1992, 48, 8891.
152. Henkel, B.; Kunath, A.; Schick, H. Liebigs Ann., 1995, 921.
153. Henkel, B.; Kunath, A.; Schick, H. J. Prakt. Chem. Chem. Ztg., 1997, 339, 434.
154. Ramaswamy, S.; Oehlschlager, A.C. Tetrahedron, 1991, 47, 1145.
155. Mori, K.; Otsuka, T. Tetrahedron, 1985, 41, 547.
156. Lin, G-Q.; Xu, W-Ch. Tetrahedron, 1996, 52, 5907.
157. Fujita, K.; Mori, K. Eur. J. Org. Chem., 2001, 493.
158. Suemune, H.; Hizuka, M.; Kamashita, T.; Sakai, K. Chem. Pharm. Bull., 1989, 37, 1379.
159. Butt, S.; Davies, H.G.; Dawson, M.J.; Lawrence, G.C.; Leaver, J.; Róberts, S.M.; Turner, M.K.; Wakefield, B.J; Wall, W.F.; Winders, J.A. J. Chem. Soc. Perkin Trans. 1, 1987, 903.
160. Sarmah, B.K.; Barua, N.C. Tetrahedron, 1993, 49, 2253.
161. Fang, J-M. Pure Appl. Chem., 1996, 68, 581.
162. Cossé A.A.; Bartelt, R.J.; James, D.G.; Petroski, R.J. J. Chem. Ecol., 2001, 27, 1841.
163. Shibata, Ch.; Mori, K. Eur. J. Org. Chem., 2004, 1083.
164. Mori, K.; Tomioka, H. Liebigs Ann. Chem., 1992, 1011.
165. Pawar, A.S.; Chattopadhyay, S.; Chattopadhyay, A.; Mamdapur, V.R. J. Org. Chem., 1993, 58, 7535.
166. Naoshima, Y.; Nakamura, A.; Nishiyama, T.; Haramaki, T.; Mende, M.; Munakata, Y. Chem. Lett., 1989, 1023.
167. Keinan, E.; Seth, K.K.; Lamed, R.; Ghirlando, R.; Singh, S.P. Biocatalysis, 1990, 3, 57.
168. Keinan, E.; Sinha, S.C.; Singh, S.P. Tetrahedron, 1991, 47, 4631.
169. Mori, K.; Amaike, M.; Oliver, J.E. Liebigs Ann. Chem., 1992, 1185.
170. Suzuki, T. Agric. Biol. Chem., 1981, 45, 1357.
171. Suzuki, T. Appl. Entomol. Zool., 1983, 18, 134.
172. Fuganti, C.; Grasselli, P.; Servi, S.; Hoegberg, H.E. J. Chem. Soc. Perkin Trans. 1, 1988, 3061.
173. Sankaranarayanan, S; Sharma, A.; Chattopadhyay, S. Tetrahedon Asymmetry, 2002, 13, 1373.
174. Chênevert, R.; Desjardins, M. J. Org. Chem., 1996, 61, 1219.
175. Kobayashi, M.; Koyama, T.; Ogura, K., Seto, S. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 1979, 22, 164.
176. Kobayashi, M.; Koyama, T.; Ogura, K., Seto, S.; Ritter, F.J.; Brüggemann-Rotgans, I.E.M. J. Am. Chem. Soc., 1980, 102, 6602.
177. Koyama, T.; Kobayashi, M.; Matsubara, M.; Ogura, K., Ritter, F.J.; Brüggemann-Rotgans, I.E.M. Nippon Kagaku Kaishi, 1983, 1377.
178. Poppe, L.; Novák L.; Kolonits, P.; Bata, A.; Szántay, C. Tetrahedron, 1988, 44, 1477.
179. Serra, S.; Fuganti, C. Helv. Chim. Acta, 2002, 85, 2489.
180. Mori, M.; Mochizuki, K.; Kohno, M.; Chuman, T.; Ohnishi, A.; Watanabe, H.; Mori, K. J. Chem. Ecol., 1986, 12, 83.
181. Pilli, R.A.; Riatto, V.B. J. Braz. Chem. Soc., 1998, 9, 571.
182. Hayakawa, R.; Shimizu, M. Synlett, 1999, 1298.
183. Ha, H-J.; Yim, Y-G. Synth. Commun., 2000, 30, 581.
184. Fujita, K.; Mori, K. Biosci. Biotech. Biochem., 2001, 65, 1429.
185. Masuda, Y.; Fujita, K.; Mori, K. Biosci. Biotech. Biochem., 2003, 67, 1744.
186. Nakazono, Y.; Komata, T.; Senda, S.; Fukusaki, E.; Yuasa, H. 1994, Jpn. Pat. JP 06007181 A2, CAN 121:7463.
187. Pilli, R.A.; Riatto, V.B. J. Braz. Chem. Soc., 1999, 10, 363.
188. Mori, K.;, Sano, S.; Yokoyama, Y.; Bando, M.; Kido, M. Eur. J. Org. Chem., 1998, 1135.
189. Lanier, G.N.; Qi, Y-T.; West, J.R.; Park, S.C.; Webster, F.X.; Silverstein, R.M. J. Chem. Ecol., 1989, 15, 1645.
190. Lin, G-Q.; Xu, W-Ch. Bioorg. Med. Chem., 1996, 4, 375.
191. Einhorn, J.; Menussieu, P.; Malosse, C.; Ducrot, P.H. Tetrahedron Lett., 1990, 31, 6633.
192. Mori, K.; Furuuchi, T.; Kiyota, H. Liebigs Ann., 1994, 971.
193. Mori, K.; Amaike, M. J. Chem Soc. Perkin Trans., 1994, 1, 2727.
194. Odinokov, V.N.; Botsman, L.P.; Saranova, L.V.; Syutkina, E.V.; Emel'yanova, G.A. Chem. Nat. Compd., 1998, 33, 687.
195. Morgani, B.; Oehlschlager, A.C.; Stokes, T.M. Tetrahedron, 1991, 47, 1611.
196. Vasil'ev, A.A.; Vlasyuk, A.L.; Gamalevich, G.D.; Serebryakov, E.P. Bioorg. Med. Chem., 1996, 4, 389.
197. Phillips, J,K.; Miller, S.P.F.; Andersen, J.F.; Fales, H.M.; Burkholder, W.E. Tetrahedron Lett., 1987, 28, 6145.
198. Sugai, T.; Sakuma, D.; Kobayashi, N.; Ohta, H. Tetrahedron, 1991, 47, 7237.
199. Poppe, L.; Novák, L.; Dévényi, J.; Szántay, C. Tetrahedron Lett., 1991, 32, 2643.
200. Sankaranarayanan, S.; Sharma, A.; Kulkarni, B.A.; Chattopadhyay, S. J. Org. Chem., 1995, 60, 4251.
201. Petschen, I.; Bosch, M.P.; Guerrero, A. Tetrahedron Asymmetry, 2000, 11, 1691.
202. Boland W.; Mertes, K.; Jaenicke, L.; Müller, D.G.; Foelster, E. Helv. Chim. Acta, 1983, 66, 1905.
203. Boland, W.; Niedermeyer, U.; Jaenicke, L.; Goerisch, H. Helv. Chim. Acta, 1985, 68, 2062.
204. Maier, I.; Müller, D.G.; Gassmann, G.; Boland, W.; Marner, F-J.; Jaenicke, L. Naturwissenschaflen, 1984, 71, 48.
205. Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett., 1996, 37, 1011.
206. Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron, 1997, 53, 145.
207. Schotten, T.; Boland, W.; Jaenicke, L. Helv. Chim. Acta, 1985, 68, 1186.
208. Yamamoto, Y.; Akakabe, Y.; Matsui, K.; Shimidzu, H.; Kajiwara, T. Z. Naturforsch., [C], 1999, 54, 1027.
209. Kajiwara, T.; Yamamoto, Y.; Akakabe, Y.; Matsui, K.; Shimizu, H.; Kawai, T. Z. Naturforsch. [C], 2003, 58, 109.
210. Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron, 1991, 47, 1215.