Convergent synthesis of the common FGHI-ring part of ciguatoxins

Tetrahedron

Volumn 62, Issue 31, 2006, Pages 7408-7435

  Takizawa, Ayumi ^a   Fujiwara, Kenshu ^a   Doi, Eriko ^a   Murai, Akio ^a   Kawai, Hidetoshi ^a   Suzuki, Takanori ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

6 exo Hydroxy epoxide opening; Ciguatoxin; Reductive etherification; The Nozaki Hiyama Kishi reaction; trans Fused tetracyclic ether

Indexed keywords

CIGUATOXIN; HYDROGEN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; EPOXIDATION; ETHERIFICATION; NONHUMAN; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 33745191187     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.05.014     Document Type: Article

References (137)

1. For reviews of ciguatoxins and related marine toxins, see:
2. Yasumoto T., and Murata M. Chem. Rev. 93 (1993) 1897
3. Scheuer P.J. Tetrahedron 50 (1994) 3
4. Murata M., and Yasumoto T. Nat. Prod. Rep. 17 (2000) 293
5. Yasumoto T. Chem. Rec. 1 (2001) 228
6. For recent reviews of ciguatera, see:
7. Lehane L., and Lewis R.J. Int. J. Food Microbiol. 61 (2000) 91
8. Lewis R.J. Toxicon 39 (2001) 97
9. Yasumoto T., Nakajima R., Bagnis R., and Adachi R. Bull. Jpn. Soc. Sci. Fish. 43 (1977) 1021
10. Recent reports for immunological detection of CTXs aiming at prevention of ciguatera intoxication:
11. Oguri H., Hirama M., Tsumuraya T., Fujii I., Maruyama M., Uehara H., and Nagumo Y. J. Am. Chem. Soc. 125 (2003) 7608
12. Hokama Y., Whang C., Chun K.F., Suma C., Higa N., Or B., Cocchetto A., and Kansky G. J. Toxcol., Toxin Rev. 22 (2003) 547
13. Nagumo Y., Oguri H., Shindo Y., Sasaki S., Oishi T., Hirama M., Tomioka Y., Mizugaki M., and Tsumuraya T. Bioorg. Med. Chem. Lett. 11 (2001) 2037
14. Pauillac S., Sasaki M., Inoue M., Naar J., Branaa P., Chinain M., Tachibana K., and Legrand A.-M. Toxicon 38 (1999) 669
15. Oguri H., Tanaka S., Hishiyama S., Oishi T., Hirama M., Tsumuraya T., Tomioka Y., and Mizugaki M. Synthesis (1999) 1431
16. Hokama Y., Nishimura K., Takenaka W., and Ebesu J.S.M. J. Nat. Toxins 7 (1998) 1
17. Scheuer P.J., Takahashi W., Tsutsumi J., and Yoshida T. Science 155 (1967) 1267
18. Tachibana, K. Ph.D. Thesis, University of Hawaii, 1980;
19. Nukina M., Koyanagi L.M., and Scheuer P.J. Toxicon 22 (1984) 169
20. Tachibana K., Nukina M., Joh Y.G., and Scheuer P.J. Biol. Bull. 172 (1987) 122
21. Satake M., Morohashi A., Oguri H., Oishi T., Hirama M., Harada N., and Yasumoto T. J. Am. Chem. Soc. 119 (1997) 11325
22. Satake M., Murata M., and Yasumoto T. Tetrahedron Lett. 34 (1993) 1975
23. For the bioactivities of ciguatoxins and related compounds, see:
24. Catterall W.A., and Risk M. Mol. Pharmacol. 19 (1981) 345
25. Bidard J.-N., Vijverberg H.P.M., Frelin C., Chungue E., Legrand A.-M., Bagnis R., and Lazdanski M. J. Biol. Chem. 259 (1984) 8353
26. Lombet A., Bidard J.-N., and Lazdanski M. FEBS Lett. 219 (1987) 355
27. Dechraoui M.-Y., Naar J., Pauillac S., and Legrand A.-M. Toxicon 37 (1999) 125 See also references cited in Ref. 2
28. For the total synthesis of CTX3C, see:
29. Hirama M., Oishi T., Uehara H., Inoue M., Maruyama M., Oguri H., and Satake M. Science 294 (2001) 1904
30. Inoue M., Uehara H., Maruyama M., and Hirama M. Org. Lett. 4 (2002) 4551
31. Maruyama M., Inoue M., Oishi T., Oguri H., Ogasawara Y., Shindo Y., and Hirama M. Tetrahedron 58 (2002) 1835
32. Uehara H., Oishi T., Inoue M., Shoji M., Nagumo Y., Kosaka M., Brazidec J.-Y.L., and Hirama M. Tetrahedron 58 (2002) 6493
33. Inoue M., Yamashita S., Tatami A., Miyazaki K., and Hirama M. J. Org. Chem. 69 (2004) 2797
34. Kobayashi S., Takahashi Y., Komano K., Alizadeh B.H., Kawada Y., Oishi T., Tanaka S., Ogasawara Y., Sasaki S., and Hirama M. Tetrahedron 60 (2004) 8375
35. Inoue M., and Hirama M. Synlett (2004) 577
36. Inoue M., and Hirama M. Acc. Chem. Res. 37 (2004) 961
37. Inoue M., Miyazaki K., Uehara H., Maruyama M., and Hirama M. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 12013
38. Hirama M. Chem. Rec. 5 (2005) 240
39. For recent synthetic studies on ciguatoxins from other groups, see:
40. Takai S., Ploypradith P., Hamajima A., Kira K., and Isobe M. Synlett (2002) 588
41. Takai S., and Isobe M. Org. Lett. 4 (2002) 1183
42. Kira K., Hamajima A., and Isobe M. Tetrahedron 58 (2002) 1875
43. Sasaki M., Ishikawa M., Fuwa H., and Tachibana K. Tetrahedron 58 (2002) 1889
44. Takakura H., Sasaki M., Honda S., and Tachibana K. Org. Lett. 4 (2002) 2771
45. Sasaki M., Noguchi T., and Tachibana K. J. Org. Chem. 67 (2002) 3301
46. Candenas M.L., Pinto F.J., Cintada C.G., Morales E.Q., Brouard I., Díaz M.T., Rico M., Rodríguez E., Rodríguez R.M., Pérez R., Pérez R.L., and Martín J.D. Tetrahedron 58 (2002) 1921
47. Bond S., and Perlmutter P. Tetrahedron 58 (2002) 1779
48. Takai S., Sawada N., and Isobe M. J. Org. Chem. 68 (2003) 3225
49. Baba T., and Isobe M. Synlett (2003) 547
50. Baba T., Huang G., and Isobe M. Tetrahedron 59 (2003) 6851
51. Tatami A., Inoue M., Uehara H., and Hirama M. Tetrahedron Lett. 44 (2003) 5229
52. Baba T., Takai S., Sawada N., and Isobe M. Synlett (2004) 603
53. Fuwa H., Fujikawa S., Tachibana K., Takakura H., and Sasaki M. Tetrahedron Lett. 45 (2004) 4795
54. Kobayashi S., Alizadeh B.H., Sasaki S.-y., Oguri H., and Hirama M. Org. Lett. 6 (2004) 751
55. Hamajima A., and Isobe M. Org. Lett. 8 (2006) 1205
56. For convergent approaches to polycyclic ether systems, see:
57. Alvarez E., Díaz M.T., Hanxing L., and Martín J.D. J. Am. Chem. Soc. 117 (1995) 1437
58. Nicolaou K.C. Angew. Chem., Int. Ed. 35 (1996) 589
59. Ravelo J.L., Regueiro A., Rodríguez E., de Vera J., and Martín J.D. Tetrahedron Lett. 37 (1996) 2869
60. Alvarez E., Pérez R., Rico M., Rodríguez R.M., and Martín J.D. Org. Chem. 61 (1996) 3003
61. Oishi T., Nagumo Y., and Hirama M. Synlett (1997) 980
62. Oishi T., Nagumo Y., and Hirama M. Chem. Commun (1998) 1041
63. Sasaki M., Inoue M., Noguchi Y., Takeichi A., and Tachibana K. Tetrahedron Lett. 39 (1998) 2783
64. Sasaki M., Fuwa H., Inoue M., and Tachibana K. Tetrahedron Lett. 39 (1998) 9027
65. Fujiwara K., Morishita H., Saka K., and Murai A. Tetrahedron Lett. 41 (2000) 503
66. Matsuo G., Hinou H., Koshino H., Suenaga T., and Nakata T. Tetrahedron Lett. 41 (2000) 903
67. Mori Y., Mitsuoka S., and Furukawa H. Tetrahedron Lett. 41 (2000) 4161
68. Kadowaki C., Chan P.W.H., Kadota I., and Yamamoto Y. Tetrahedron Lett. 41 (2000) 5769
69. Díaz M.T., Pérez R.L., Rodríguez L., Ravelo J.L., and Martín J.D. Synlett (2001) 345
70. Suzuki K., and Nakata T. Org. Lett. 4 (2002) 2739
71. Kadota I., Ohno A., Matsuda K., and Yamamoto Y. J. Am. Chem. Soc. 124 (2002) 3562
72. Inoue M., Wang G.X., Wang J., and Hirama M. Org. Lett. 4 (2002) 3439
73. Oishi T., Watanabe K., and Murata M. Tetrahedron Lett. 44 (2003) 7315
74. Inoue M., Wang J., Wang G.-X., Ogasawara Y., and Hirama M. Tetrahedron 59 (2003) 5645
75. Sasaki M., and Fuwa H. Synlett (2004) 1851
76. Kadota I., and Yamamoto Y. Acc. Chem. Res. 38 (2005) 423
77. Inoue M. Chem. Rev. 105 (2005) 4379
78. Recent reviews for the synthesis of polycyclic ethers:
79. Nakata T. Chem. Rev. 105 (2005) 4314
80. Inoue M. Chem. Rev. 105 (2005) 4379
81. For the synthetic studies on ciguatoxins in our laboratory, see:
82. Oka T., and Murai A. Chem. Lett. (1994) 1611
83. Oka T., Fujiwara K., and Murai A. Tetrahedron 52 (1996) 12091
84. Atsuta H., Fujiwara K., and Murai A. Synlett (1997) 307
85. Oka T., Fujiwara K., and Murai A. Tetrahedron Lett. 38 (1997) 8035
86. Oka T., and Murai A. Tetrahedron 54 (1998) 1
87. Oka T., Fujiwara K., and Murai A. Tetrahedron 54 (1998) 21
88. Fujiwara K., Saka K., Takaoka D., and Murai A. Synlett (1999) 1037
89. Fujiwara K., Tanaka H., and Murai A. Chem. Lett. (2000) 610
90. Fujiwara K., Takaoka D., Kusumi K., Kawai K., and Murai A. Synlett (2001) 691
91. Fujiwara K., Koyama Y., Doi E., Shimawaki K., Ohtaniuchi Y., Takemura A., Souma S., and Murai A. Synlett (2002) 1496
92. Fujiwara K., Koyama Y., Kawai K., Tanaka H., and Murai A. Synlett (2002) 1835
93. Tanaka H., Kawai K., Fujiwara K., and Murai A. Tetrahedron 58 (2002) 10017
94. Fujiwara K., Goto A., Sato D., Ohtaniuchi Y., Tanaka H., Murai A., Kawai H., and Suzuki T. Tetrahedron Lett. 45 (2004) 7011
95. Takemura A., Fujiwara K., Murai A., Kawai H., and Suzuki T. Tetrahedron Lett. 45 (2004) 7567
96. Takemura A., Fujiwara K., Shimawaki K., Murai A., Kawai H., and Suzuki T. Tetrahedron 61 (2005) 7392
97. Domon D., Fujiwara K., Ohtaniuchi Y., Takezawa A., Takeda S., Kawasaki H., Murai A., Kawai H., and Suzuki T. Tetrahedron Lett. 46 (2005) 8279
98. Domon D., Fujiwara K., Murai A., Kawai H., and Suzuki T. Tetrahedron Lett. 46 (2005) 8285
99. Takizawa A., Fujiwara K., Doi E., Murai A., Kawai H., and Suzuki T. Tetrahedron Lett. 47 (2006) 747
100. Ogura K., and Tsuchihashi G. Tetrahedron Lett. 13 (1972) 2681
101. Herrmann J.L., Richman J.E., Wepplo P.J., and Schlessinger R.H. Tetrahedron Lett. 14 (1973) 4707
102. The position numbering is according to that of CTX3C.
103. Nicolaou K.C., Hwang C.K., and Nugiel D.A. J. Am. Chem. Soc. 111 (1989) 4136
104. A similar ring closure of the G-ring part by reductive etherification was reported by the Isobe group, where the cyclization of a tricyclic compound corresponding to the EF-H-ring part having 26-keto and 31-hydroxy groups was successfully performed:. Takai S., Sawada N., and Isobe M. J. Org. Chem. 68 (2003) 3225
105. Okude Y., Hirano S., Hiyama T., and Nozaki H. J. Am. Chem. Soc. 99 (1977) 3179
106. Jin H., Uenishi J., Christ W.J., and Kishi Y. J. Am. Chem. Soc. 108 (1986) 5644
107. For successful synthesis of a Z-iodoolefin, see:
108. Smith III A.B., Beauchamp T.J., LaMarche M.J., Kaufman M.D., Qiu Y., Arimoto H., Jones D.R., and Kobayashi K. J. Am. Chem. Soc. 122 (2000) 8654
109. Sawada D., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 122 (2000) 10521
110. See, also:
111. Tanino K., Arakawa K., Satoh M., Iwata Y., and Miyashita M. Tetrahedron Lett. 47 (2006) 861
112. Mori Y., Yaegashi K., and Furukawa H. J. Am. Chem. Soc. 118 (1996) 8158
113. Carling R.W., and Holmes A.B. Tetrahedron Lett. 27 (1986) 6133
114. Kotsuki H., Kadota I., and Ochi M. Tetrahedron Lett. 31 (1990) 4609
115. Negishi E., and Yoshida T. Tetrahedron Lett. 21 (1980) 1501
116. 2ZrHCl), see:. Kiyotsuka Y., Igarashi J., and Kobayashi Y. Tetrahedron Lett. 43 (2002) 2725
117. Hart D.W., and Schwartz J. J. Am. Chem. Soc. 96 (1974) 8115
118. Schwartz J., and Labinger J.A. Angew. Chem., Int. Ed. Engl. 15 (1976) 333
119. cf. Nocolaou K.C., Veale C.A., Hwang C.-K., Hutchinson J., Prasad C.V.C., and Ogilvie W.W. Angew. Chem., Int. Ed. Engl. 30 (1991) 299
120. Dess D.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155
121. Dess D.B., and Martin J.C. J. Am. Chem. Soc. 113 (1991) 7277
122. Corey E.J., Narasaka K., and Shibasaki M. J. Am. Chem. Soc. 98 (1976) 6417
123. Crimmins M.T., and Tabet E.A. J. Am. Chem. Soc. 122 (2000) 5473
124. 1H NMR data of MTPA esters of 22 are described in Section 7. Ohtani I., Kusumi T., Kashuman Y., and Kakisawa H. J. Am. Chem. Soc. 113 (1991) 4092
125. Kim S., and Ahn K.H. J. Org. Chem. 49 (1984) 1717
126. Gemal A.L., and Luche J.L. J. Am. Chem. Soc. 103 (1981) 5454
127. Krishnamurthy S., and Brown H.C. J. Am. Chem. Soc. 98 (1976) 3383
128. Tanaka S., Yamamoto H., Nozaki H., Sharpless K.B., Michaelson R.C., and Cutting J.D. J. Am. Chem. Soc. 96 (1974) 5254
129. Miyashita M., Yoshikoshi A., and Grieco P.A. J. Org. Chem. 42 (1977) 3772
130. Nicolaou K.C., Prasad C.V.C., Hwang C.-K., Duggan M.E., and Veale C.A. J. Am. Chem. Soc. 111 (1989) 5321
131. Fujiwara K., Saka K., Takaoka D., and Murai A. Synlett (1999) 1037
132. Mancuso A.J., Huang S.-L., and Swern D. J. Org. Chem. 43 (1978) 2480
133. Evans D.A., Gauchet-Prunet J.A., Carreira E.M., and Charette A.B. J. Org. Chem. 56 (1991) 741
134. Chen K.-M., Hardtmann G.E., Prasad K., Repic O., and Shapiro M.J. Tetrahedron Lett. 28 (1987) 155
135. Gaunt M.J., Yu J., and Spencer J.B. J. Org. Chem. 63 (1998) 4172
136. Xia J., Abbas S.A., Locke R.D., Piskorz C.F., Alderfer J.L., and Matta K.L. Tetrahedron Lett. 41 (2000) 169
137. Wright J.A., Yu J., and Spencer J.B. Tetrahedron Lett. 42 (2001) 4033