Asymmetric synthesis of optically active 1,4-dihydropyridines as calcium antagonist

Current Organic Chemistry

Volumn 3, Issue 1, 1999, Pages 77-106

  Achiwa, Kazuo ^a   Kato, Tatsuhisa ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CALCIUM; DISEASES;

ASYMMETRIC SYNTHESIS; CARDIOVASCULAR DISEASE; DIESTERS; DIHYDROPYRIDINES; LIPASE-CATALYZED RESOLUTION; OPTICALLY ACTIVE; PHARMACOLOGICAL ACTIVITY; RESOLUTION SYNTHESIS;

SYNTHESIS (CHEMICAL);

1,4 DIHYDROPYRIDINE 3,5 DICARBOXYLIC DIESTER DERIVATIVE; 1,4 DIHYDROPYRIDINE DERIVATIVE; CALCIUM ANTAGONIST; CARDIOVASCULAR AGENT; THALIDOMIDE; UNCLASSIFIED DRUG;

CARDIOVASCULAR EFFECT; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; OPTICAL RESOLUTION; OPTICAL ROTATION; REVIEW;

EID: 0032969532     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (181)

1. A. Hantzsch, Justus Liebigs Ann. Chem. 1882, 215, 1-82.
2. a). F. Bossert, W. Vater, Med. Res. Rev., 1989, 9, 291-324
3. b) F. Bossert, W. Vater, DE 1493677,1964, Bayer AG
4. c)F. Bossert, W. Vater, Naturwissenschaften, 1971, 58, 578
5. d) B. Loev, R. E. Tedeschi, US 351184, Smith Kline and French
6. e) B. Loev, S.J. Ehrreich, R. E. Tedeschi, J. Pharm. Pharmacol., 1972, 24, 917-918.
7. f) B. Loev, MM Goodman, K.M., Sander, R. Tedeschi, E. Macko, J. Med. Chem., 1974, 17, 956-965.
8. g) A. Fleckenstein, H. Tritthart, H. J. Döring, K. Y. Byon, Arzneim. Forsch., 1972, 22, 22-23.
9. h) A. Fleckenstein, G. Gru n, Arzneim Forsch., 1972, 22, 334-344.
10. i) V. Kastrons, R. Vitolins, G. Duburs, Khim Farm. Zh. 1990, 24, 14-21.
11. j) D. J. Triggle, D. A. Langs, R. A. Janis, Med. Res. Rev., 1989, 9, 123-180.
12. k) "Drug action and cellular calcium regulation" : R. A. Janis, P. Silver, D. J. Triggle, Adv. Drug. Res., 1987, 16, 309-591.
13. l) M. Ohtuska, M. Yokota, I. Kodama, K. Yamada, S. Shibata, Gen. Pharmacol., 1989, 20, 539-556.
14. m) A. Sausins. G. Durburs, Heterocycles, 1988, 27, 269-314.
15. n) F. Bessert, H. Meyer, E. Wehinger, Angew. Chem., 1981, 93, 755-763; Angew Chem. Int. Ed. Engl., 1981, 20, 762-769.
16. n) F. Bessert, H. Meyer, E. Wehinger, Angew. Chem., 1981, 93, 755-763; Angew Chem. Int. Ed. Engl., 1981, 20, 762-769.
17. o) D. M. Stout, A. I. Meyers, Chem. Rev., 1982, 82, 223-243
18. p) J. Khuthan, A. Kurfürst, Ind. Eng. Chem. Prod. Res. Dev., 1982, 21, 191-261.
19. q) U. Eisner, J. Khuthan, Chem. Rev., 1972, 72, 1-42.
20. r) D. D. Freedman, D. D. Waters, Drugs, 1987, 34, 578-598.
21. s) A. Fleckenstein. Calcium and Heart, Proceedings of the Meeting of European Section of the International Study for Research in Cardiac Metabolism (ed. by P. Harris, & L. Ople.), 135, Academic Press, New York, 1970.
22. t) T. Rosenthal, D. Ezra Drug Saf., 1995, 13, 157-187
23. u) B. Chamontin, J. Amar, J. Hum. Hypertents, 9 Suppl. 4, 1995, S35-39.
24. v) J. D. Cohen, Curr. Opin. Nephrol. Hypertents, 1996, 5, 214-218.
25. H. Abe, K. Katada, M. Orita, M. Nishikibe, J. Pharm. Pharmacol., 1991, 43, 22-26.
26. a) A. P. Sen, P. Boksa, R. Quirion, Brain Res., 1993, 611, 216-221.
27. b) H. J. Koch, H. R. Dinse, Meth. Find. Bxp. Clin. Pharmacol., 1994, 16, 687.
28. a) S. Fernandez-Gallardo, M. D.P. Ortega, J. G. Priego, M. F. D. Casajuana, C. Sunkel, M. S. Crespo, J. Pharmacol. Exp. Ther., 1990, 255, 34-39.
29. b) M. P. Ortega, M. D. C. Garcia, M.A. Gijoln, M.F. Casa-Juana, J.G. Prie, M.S. Crespo, C. Sunkel, Ibib, 1990, 255, 28-33.
30. c) C.E. Sunkel, M.F. Casa-Juana, F. J. Cillero, J.G. Priego M.P. Ortega, J. Med. Chem., 1988, 31, 1886-1890
31. d) M. J. Fray, D. J. Bull, K. Cooper, M. J. Parry, M. H. Stefaniak, J. Med. Chem., 1995, 38, 3524-3535.
32. e) M. J. Fray, K. Cooper, M. J. Parry, K. Richardson, J. Steele, J. Med. Chem., 1995, 38, 3514-3523.
33. f) A. F. Rump, M. Boller, R. Berkels, R. Rosen, U. Fricke, W. Klaus, Gen. Pharmacol., 1994, 25, 447-450
34. g) R. E. Catalan, A. M. Martinez, M. D Argones, E Garde, M. Lombardia, P. Ortega, J. Biochem. Tokyo, 1993, 113, 450-455.
35. h) R. E. Catalan, A. M. Martinez, M.D. Argones, M. Lombardia, E. Garde, Eur. J. Pharmacol., 1995, 290, 183-188.
36. a) H. Suzuki, Iyaku Journal, 1991, 27, 519.
37. b) JP S64-31780, 1989.
38. c) JP S64-31781, 1989.
39. d) K. Ohsumi, K. Ohishi, Y. Morinaga, R. Nakagawa, Y. Suga, T. Sekiyama, Y. Akiyama, T. Tsuji, T. Tsuruo, Chem. Pharm. Bull., 1995, 43, 818-828.
40. a) K. Ohishi, Y. Morinaga, K. Ohsumi, R. Nakagawa, Y. Suga, T. Tsuji, Y. Akiyama, T. Tsuruo, Cancer-Chemother-Pharmacol., 1996, 38, 446-452.
41. b, F. Schroder, S. Herizg Arzneimittelforschung, 1993, 43, 1148-1151.
42. c) R. Gaggi R. Cont, A. M. Gianni, Gen Pharmacol, 1993, 24, 1091-1096.
43. d) P. Cozzi, G. Carganico, D. Fusar, M. Grossoni, M. Menicincheri, V. Pinciroli, R. Tonani, F. Vaghi, P. Salvati, J. Med. Chem., 1993, 36, 2964-2972.
44. e) D. Tirzite, G. Tirzitis B. Vigante, G. Dubers, Biochem. Pharmacol., 1993, 46, 773-775.
45. f) J. L. Jiang, A.M. van Rhee, N. Melman, X. D. Ji, K. A. Jacobson, J. Med. Chem., 1996, 39, 4667-4675.
46. a)Siegfried Goldman and Jürgen Stoltefuss, Angew. Chem. Int. Ed. Engl., 1991, 30, 1559-1578.
47. b) K. Meguro, M. Aizawa, T. Sohda, Y. Kawamatsu, A. Nagaoka, Chem. Pharm. Bull., 1985, 33, 3787-3797.
48. c) M. Kajino, Y. Wada, Y. Nagai, A. Nagaoka, K. Meguro, Chem. Pharm. Bull., 1989, 37, 2225-2228.
49. d) T. Takenaka, S. Usuda, T. Nomura, H. Maeno. T. Sado, Arzneim. Forsch., 1976, 26, 2172-2178.
50. e) K. Tamazawa, H. Arima, T. Kojima, Y. Isomura, M. Iwanani, K. Okuda, T. Takenaka, M. Murakami, Chem. Pharm. Bull., 1980, 28, 2809-2812.
51. g) T. Furuta, S. Shibata, I. Kodama, K. Yamda, J. Cardiovasc. Pharmacol., 1983, 5, 836-841.
52. h) Y. Sato, K. Okumura, Y. Shiokawa. Chem. Pharm. Bull., 1992, 40, 1799-1807.
53. i) K. Suzuki, J. Nagura, K. Shiratori, B. Maruyama, N. Harada, T. Miyano, K. Takeya, J. Phacobio-Dyn., 1989, 12, 293-298.
54. j) M. Nishikibe, J. Pharmacol. Exp. Ther., 1988, 246, 719-725.
55. k) R Sakoda, y. Kamikawaji, K. Seto, Chem. Pharm. Bull., 1992, 40, 2362-2369.
56. l) Idem, Ibid. 1992, 40, 2370-2376.
57. m) R. Sakoda, H. Matsumoto, K. Seto, Ibid. 1992, 40, 2377-2381.
58. n) I. Adachi, T. Yamamori, Y. Hiramatsu, K. Sakai, S. Mihara, M. Kawakami, M. Masui, O. Uno, M. Ueda, Chem. Pharm. Bull., 1988, 36, 4389-4402.
59. a) B. Loev, M. M. Goodmann, J. Heterocycl. Chem., 1975, 12, 363-365.
60. b) E. Wehinger, F. Bossert, DE 2847237,1980, Bayer AG.
61. c) G. Franckowiak, H. Böshagen, F. Bossert, S. Goldmann, H. Meyer, E. Wehinger, J. Stoltefuss, M. Schramm, G. Thomas, R. Towart DE 3130041, 1981, Bayer AG.
62. d) H. Kühnis, DE 3445356, 1985, Ciba-Geigy AG.
63. e) H. Meyer, E. Wehinger, F. Bossert, D. Scherling, Arzneim. Forsch., 1983, 33, 106-112.
64. f) R. P. Hof, U. T. Rüegg, A. Hof, A. Vogel, J. Cardiovasc. Pharmacol, 1985, 7, 689.
65. a) K. Suzuki, T. Shiraishi, Y. Yoshida, T. Matsumoto, M. Iwamoto, Y. Motoyoshi, H. Niwa, Y. Inoue, EP 118120, 1984, Nikken Chem.
66. b) A. Vogel, DE 3320616, 1983, Sandoz.
67. c) B. Kohl, W. R. Ulrich, D. Flockerzi, EP 394243, 1987, Byk Gulden Lomberg
68. d) J. J. Suh, Y. H. Hong, Yakhak Hoechi, 1989, 33, 219-225; see also Chem. Abstr., 1990, 112, 235135.
69. d) J. J. Suh, Y. H. Hong, Yakhak Hoechi, 1989, 33, 219-225; see also Chem. Abstr., 1990, 112, 235135.
70. e) J. J. Suh, Y. H. Hong, Yakhak Hoechi, 1989, 33, 80-86; see also Chem. Abstr., 1990, 112, 76894.
71. e) J. J. Suh, Y. H. Hong, Yakhak Hoechi, 1989, 33, 80-86; see also Chem. Abstr., 1990, 112, 76894.
72. f) Y. K. Shim, S. H. Lee. J. S. Kang. W., J. Kim, Taehan Hwahaknoe Chi, 1988, 32, 144-148; see also Chem. Abstr., 1989, 110, 8013.
73. f) Y. K. Shim, S. H. Lee. J. S. Kang. W., J. Kim, Taehan Hwahaknoe Chi, 1988, 32, 144-148; see also Chem. Abstr., 1989, 110, 8013.
74. M. Iwanami, T. Shibanuma, M. Fujimoto, R. Kawai, K. Tamazawa, T. Takenaka, K. Takahashi, M. Murakami, Chem. Pharm. Bull., 1979, 27, 1426-1440.
75. G.Genain, EP 273349, 1987 Syntex.
76. a) M. Kajino, Y. Wada, Y. Nagai, A. Nagaoka, K. Meguro, Chem. Pharm. Bull., 1989, 37, 2225-2228.
77. b) A. Ashimori, T. Uchida, Y. Ohtaki, M. Tahaka, K. Ohe, C. Fukaya, M. Watanabe, M. Kagitani, K. Yokoyama, Ibid, 1991, 39, 108-111.
78. C. A. Gandolfi, M. Frigerio C. Riva, A. Zaliani, G. Long, R. Di Domenico, EP 383320, 1990, Boehringer Biochemia Robin.
79. a) E. Wehihger, H. Meyer, F. Bossert, W. Vater, R. Towart, K. Stoepel, S. Kazda, DE 2935451, 1981 Bayer AG: JP S 56-36355, 1981.
80. b) E. Wehihger, H. Meyer JP S 61-41063, 1980; H6-35438, 1994.
81. c) E. Wehihger, H.Meyer, JPH6-41063, 1994.
82. d) J. E. Arrowsmith, EP 331315, 1989, Pfizer Ltd.
83. e) J. E. Arrowsmith, S. F. Campbell, P. E. Cross, J. K. Stubbs, R. A. Surges, D. G. Gardiner, K. J. Blackburn, J. Med. Chem., 1986, 29, 11696-1702.
84. f) M. Kamikawaji, K. Seto, R. Sakota, JP 01113398, 1998, Nissan Chem. Ind.; see also Chem Abstr., 1990, 112, 25675
85. f) M. Kamikawaji, K. Seto, R. Sakota, JP 01113398, 1998, Nissan Chem. Ind.; see also Chem Abstr., 1990, 112, 25675
86. g) J. L. Peglion, Y. M. Gargouil, J. P. Vilanie, EP 406504, 1991, ADIR et Comp.
87. h) A. Vogel, DE 3305577, 1983, Sandoz.
88. i) H. Matsumoto, M. Klamikawa, K. Seto, R. Sakota, S. Tanaka, JP 02011592, 1990, Nissan Chem Ind. : also Chem. Abstr., 1990, 113, 59536.
89. i) H. Matsumoto, M. Klamikawa, K. Seto, R. Sakota, S. Tanaka, JP 02011592, 1990, Nissan Chem Ind. : also Chem. Abstr., 1990, 113, 59536.
90. j) G. Franckowiak, R. Grosser, G. Thomas, M. Schramm, R. Gross, DE 3447169, 1986 Bayer AG.
91. a) B. Lamm, R. Simonsson, S. Sundell, Tetrahedron Lett. 1989, 30, 6423-6426.
92. b) J. Stoltefuss, M. Becham. R. Gross, S. Hebisch, M. Schramm, EP347678, 1989, Bayer AG.
93. c) A. J. G. Baxter, J. Dixon, K. J. Gould. T. McInally, A. C. Tinker, EP 125803, 1984, Fisons.
94. a) H. Yamaguchi, H. Sugano, M. Hasegawa, K. Kataoka, Y. Miyaoka, T. Kishimoto, JP H1-104046, 1989; H6-2738, 1994
95. b) W. Hermann, J. Keinschroth, K. Steiner, EP 385423, 1990, Gödecke AG.
96. c) H. yamaguchi, M. Hasegawa, H. Sugano, JP 01029359, 1989, Teijin Ltd.; see also Chem. Abstr., 1989, 111, 97095.
97. c) H. yamaguchi, M. Hasegawa, H. Sugano, JP 01029359, 1989, Teijin Ltd.; see also Chem. Abstr., 1989, 111, 97095.
98. a) K. Kataoka, H. Sugano, H. Yamaguchi, JP H2-212474,1990.
99. b) A. Kakuini, H. Ikawa, N. Kobayashi, Y. Isowa, JP S63-208573, 1988; H6-43397, 1994.
100. c) H. Ikawa, A. Kakuiri, Y. Sekine, JP H3-20271, 1991.
101. d) H. Ikawa, A. Kakuiri, Y. Konagai, T. yamaura, N. Kase, JP H5-78319, 1993.
102. e) K. Tamazawa, H. Arima, T. Kojima, O. Inagaki, M. Terai, J. Med. Chem., 1986. BayerAG.
103. g) D. Enders S. Müller, A. S. Demir, Tetrahedron Lett., 1988, JP 63208537, 1988, Fujirebio; see also Chem. Abstr., 1989, 110, 95014.
104. g) D. Enders S. Müller, A. S. Demir, Tetrahedron Lett., 1988, JP 63208537, 1988, Fujirebio; see also Chem. Abstr., 1989, 110, 95014.
105. "Drug action and cellular calcium regulation"; R. A. Janis, P. Silver, D. J. Tringgle, Adv. Drug Res., 1987, 16, 309-591.
106. a) E. Booker, U. Eisner, J. Chem. Soc. Perkin Trans., 1, 1975, 929-931.
107. b) S. Yamada, Y. Kikugawa, Chem Ind. (London). 1966, 2169-2170.
108. c) A. I. Meyers, T. Oppenlaender, J. Chem. Soc. Chem. Commun. 1986, 920-921.
109. d) A. I. Meyers, T. Oppenlaender, J. Am. Chem. Soc., 1986, 108, 1989-1996
110. e) C-Y. Cheng, J-Y. Chen, M-J. Lee, Heterocycles, 1996, in press.
111. a) G. Blaschke, F. Donow, DE 25500523, 1976, Merck Patent GmbH.
112. b) U. Schwartz, R. Grosser, K. E. Piejko, B.Bömer, D. Arlt, DE 3534356, 1987, Bayer AG.
113. c) D. W. Armstrong, T. J. Ward, R. D. Armstrong, T. E. Beesley, Science (Washington DC), 1986, 232, 1130-1135.
114. d) A. M. Stalcup, S. C. Chang, D. W. Armstrong, J. Pitha, J. Chromatogr., 1990, 573, 181-194.
115. e) Y. Tokuma, T. Fujiwara, H. Noguchi, J. Pharm. Sci., 1987, 76, 310-313.
116. f) E. Delee, I. Jullien, L. Le Garrec, J. Chromatogr., 1988, 450, 191-197.
117. g) Y. Okamoto, R. Aburatani, K. Hatano, K. Hatada, J. Liq. Chromatogr., 1988, 11, 2417-2163.
118. h) Y Okamoto, R. Aburatani, K. Hatano, K. Hatada, Chem. Lett., 1989, 715-719.
119. i) Y. Okamoto, R. Aburatani, K. Hatano, K. Hatada, N. Inostume, M. Nakano, J. Chromatogr., 1990, 513, 375-378.
120. j) P. A. Soons, M. C. M. Roosemalen, D. D. Breimer, J. Chromatogr.,1990, 528, 343-358.
121. a) H. Ebiike, Y. Terao, K. Achiwa, Tetrahedron Lett., 1991, 32, 5805-5808
122. b) X. K. Holdgru:n, C. J. Sih, Tetrahedron Lett., 1991, 32, 3465-3468.
123. a) P. A. Fitzpatrick, A. M. Klibanov, J. Am. Chem. Soc., 1991, 113, 3166-3171.
124. b) A. Zaks, A. Klibanov, Proc. Natl. Acad. Sci. U.S.A., 1985, 82, 3192-3196.
125. c) H. Kitaguchi, P.A. Fitzpatrick, J. E. Huber, A. M. Klibanov, J. Am. Chem. Soc., 1991, 111, 3094-3095.
126. d) J. S. Dordick, Enzyme Microb. Technol., 1989, 11, 194.
127. e) S. Parida, J. S. Dordick, J. Am. Chem. Soc., 1991, 113, 2253-2259.
128. f) M. N. Gupta, Eur. J. Biochem., 1992, 203, 25-32.
129. g) F. Terradas, M. Teston-Henry, P. A. Fitzpatrick, A. M. Klibanov, J. Am. Chem. Soc., 1993, 115, 390-396.
130. h) K. Nakamura, M. Kinoshita, A. Ohno,Tetrahedron, 1994, 50, 4681-4690.
131. i) B. Herradon, S. Valvaerde, Tetrahedron Asymmetry, 1994, 5, 1479-1500.
132. a) T. M. Stokes, A. C. Oehlschlager, Tetrahedron Lett, 1987, 28 2091-2094.
133. b) K. Kitaguchi, I. Itoh, M. Ono, Chem. Lett., 1990, 32, 1203-1206.
134. K. Nakamura, Y. Takabe, T. Kitayama, A. Ohno, Tetrahedron Lett., 1991, 32, 4941-4944.
135. S. Tawaki, A. M., Klibanov, J. Am. Chem. Soc., 1992, 114, 1882-1884.
136. a) J. A. Riddick, E. E. Toops, Jr. "TECHNIQUES OF ORGANIC CHEMISTRY volume VII, ORGANIC SOLVENTS" Second Edition, Inter-science Publishers, Inc., New York, 1995.
137. b) C. Laane, S. Boeren, K. Vos, C. Veeger, Biotechnology and Bioengineering, 1987, 30, 81-87.
138. a) Y. Hirose, K. Kariya, I. Sasaki, Y. Kurono, H. Ebiike, K. Achiwa, Tetrahedron Lett., 33, 1992, 7157-7160.
139. b) Y. Hirose, K. Kariya, I. Sasaki, K. Achiwa, JP H6-205686, 1994.
140. Y. Hirose, "Basic Studies for the Industrialization of Protease and Lipase-catalyzed Asymmetric Synthesis of Optically Active 1,4-Dihydropyridine", 1995, pp. 41-42.
141. Y. Hirose, "Basic Studies for the Industrialization of Protease and Lipase-catalyzed Asymmetric Synthesis of Optically Active 1,4-Dihydropyridine", 1995, pp. 39.
142. a) Y. Hirose, K. Kariya, I. Sasaki, Y. Kurono, K. Achiwa, Tetrahedron Lett., 1993, 34, 3441-3444.
143. b) Y. Hirose, I. Sasaki, K. Achiwa, JP H6-107636,1994.
144. c) M. Itoh, M. Sugiura, Yakusi, 1968, 88, 1576-1582.
145. d) Idem, Ibid. 1968, 88 1583-1590.
146. e) Idem, Ibid., 1968, 88, 1591-1595.
147. C. D. Reeve, D. H. G. Crout, K. Cooper, M. J. Fray, Tetrahedron : Asymmetry, 1992, 3, 785-794.
148. a) T. Adachi, M. Ishii, Y. Ohta, K. Ogawa, K. Hanada, Tetrhedron: Asymmetry, 1993, 4, 2061-2068.
149. b) T. Adachi, M. Ikeda, T. Hadati K. Hanada, JP H4-299994,1992.
150. c) T. Adachi, M. Ikeda, T. Hadati, K. Hanada, JP H5-84089, 1993.
151. d) K. Isshiki, T. Nakajima, T. Yoshioka, JP-H6-90790, 1994.
152. e) K. Isshiki, T. Nakajima, H. Tanaka, T. Yoshioka, JP H6-279409, 1994.
153. M. Kajino, Y. Wada, Y. Nagai, A. Nagaoka, K. Meguro, Chem. Pharm, Bull., 1989, 37, 2225-2228.
154. a) Y. Hirose, K. Kariya, I. Sasaki, Y. Kurono, K. Achiwa, Tetrahedron Lett., 1993, 34, 5915-5918.
155. b) Y. Hirose, K. Kariya, I. Sasaki, K. Achiwa, JP H5-243913, 1994.
156. a) A. Kojima, N. Takenaka, JP S57-30111, 1982.
157. b) K. Tamazawa, A. Kojima, H. Arima, Y. Murakami, Y. Isomura, K. Takanobu, JP S60-231673,1995.
158. c) K. Tamazawa, A. Kojima, H. Arima, Y. Murakami, Y. Isomura, K. Takanobu, JP S60-258179, 1985
159. d) H. Arima, K. Tamazawa, JP S62-174071, 1987.
160. H. Ebiike, K. Maruyama, K. Achiwa, Chem. Pharm. Bull. 1992, 40, 1083-1085.
161. H. Ebiike, K. Maryama, K. Achiwa, Tetrahedron: Asymmetry, 1992, 3, 1153-1156.
162. H. Ebiike, Y. Ozawa, K. Achiwa, Y. Hirose, K. Kariya, I. Sasaki, Y. Kurono, Heterocylces, 1993, 135, 26-129.
163. a) Y. Yamazaki, K. Achiwa, Heterocycles, 1996, 42, 214-216.
164. b) Y. Yamazaki, H. Ebiike, K. Achiwa, Chem. Pharm. Bull., 1994, 42, 1968-1970.
165. H. Ebiike, K. Achiwa, Tetrahedron: Asymmetry, 1994, 5, 1447-1450.
166. H. Ebiike, Y. Yamazaki, K. Achiwa, Chem. Pharm. Bull., 1995, 43, 1251-1253.
167. T. Kato, M. Tejima, H. Ebiike, K. Achiwa, Chem. Pharm. Bull., 1996, 44, 1132-1134.
168. a) E. J. Gilbert, Enzyme Microb. Technol., 1993, 15, 634.
169. b) Y. Nakanishi, Y. Kurono, Y. Koide, T. Beppu, JP H3-87187, 1991; EP 0331376, 1989.
170. c) Y. Nakanishi, Y. Kurono, S. Hirose, JP H6-153965, 1994.
171. a) Z-F. Xie, H. Suemune, K. Sakai, Tetrahedron: Asymmetry, 1990, 1, 395-402
172. b) Idem, Ibid, 4, 1993, 973-980.
173. c) Z-F, Xie, Ibid., 1991, 2, 733-750.
174. d) R. J. Kazlauskas, A. N.E. Weissflosh, A. T. Rappaport, L. A. Cussi, J. Org. Chem., 1991, 56, 2656-2665.
175. e) E. J. Toone, M. J. Werth, J. B. Jones, J. Am. Chem. Soc., 1990, 12, 4946-4952.
176. f) J. B. Jones, Can. J. Chem., 1993, 771, 273-1282.
177. M. E. M. Noble, A. Cleasby, L. N. Johnson, M. R. Egmond, L. G. J. Frenken, FEBS LETT., 1993, 331, 123-128.
178. Y. Hirose, K. Kariya, Y. Nakanishi, Y. Kurono, K. Achiwa, Tetrahedron Lett., 1995, 36, 1063-1066.
179. Y. Nakanishi, K. Kariya, Y. Hirose, I. Sasaki, JP H7-30093, 1995.
180. a) S-I. Ozaki, P. R. Ortiz de Motellano., J. Am. Chem. Soc. 1994, 116, 4487-4488.
181. b) R. Sakowics, M. Gold, J. B. Jones, J. Am. Chem. Soc., 1995, 117, 2387-2394.