Recent advances in the syntheses of biologically active natural products using biocatalyst

Heterocycles

Volumn 78, Issue 7, 2009, Pages 1667-1713

  Akita, Hiroyuki ^a  

^a TOHO UNIVERSITY   (Japan)

Author keywords

Asperlin; Chuangxinmycin; Cystothiazole; Indolmycin; Myxothiazole; Oudemansin

Indexed keywords

EID: 70349336142     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-09-652     Document Type: Review

References (104)

1. Clough J.M. Natural Product Reports (1993) 565
2. Sauter H., Steglich W., and Anke T. Angew. Chem. Int. Ed. (1999) 1328
3. Anke T., Hecht H.J., Schramm G., and Steglich W. J. Antibiot. 32 (1979) 1112
4. Anke T., Besl H., Mocek U., and Steglich W. J. Antibiot. 36 (1983) 661
5. Anke T., Werle A., Bross M., and Steglich W. J. Antibiot. 43 (1990) 1010
6. Akita H., Koshiji H., Furuich A., Horikoshi K., and Oishi T. Tetrahedron Lett. 24 (1983) 2009
7. Nakata T., Kuwabara T., Tani Y., and Oishi T. Tetrahedron Lett. 23 (1982) 115
8. Akita H., Furuichi A., Koshiji H., Horikoshi K., and Oishi T. Tetrahedron Lett. 23 (1982) 4051
9. Akita H., Furuichi A., Koshiji H., Horikoshi K., and Oishi T. Chem. Pharm. Bull. 31 (1983) 4384
10. Dale J.A., and Mosher H.S. J. Am. Chem. Soc. 95 (1973) 512
11. Nakata T., and Oishi T. T. Tetrahedron Lett. 21 (1980) 1641
12. Akita H., Matsukura H., and Oishi T. Tetrahedron Lett. 27 (1986) 5241
13. Akita H., Matsukura H., and Oishi T. Tetrahedron Lett. 27 (1986) 5397
14. Kallmerten J., and Wittman M.D. Tetrahedron Lett. 27 (1986) 2443
15. Roush W.R., Blizzard T.A., and Basha F.Z. Tetrahedron Lett. 23 (1982) 2331
16. Akita H., Todoroki R., Endo H., Ikari Y., and Oishi T. Synthesis (1993) 513
17. Mukaiyama T., and Murakami M. Chem. Lett. (1981) 1129
18. Akita H., Kawaguchi T., Enoki Y., and Oishi T. Chem. Pharm. Bull 38 (1983) 323
19. Akita H., Umezawa I., Nozawa M., and Nagumo S. Tetrahedron: Asymm. 4 (1993) 757
20. Umezawa I., Nozawa M., Nagumo S., and Akita H. Chem. Pharm. Bull. 43 (1995) 1111
21. Akita H., Chen C.-Y., and Nagumo S. Tetrahedron: Asymm. 5 (1994) 1207
22. Akita H., Chen C.-Y., and Nagumo S. J. Chem. Soc. Perkin Trans. I (1995) 2159
23. Kato K., Ono M., and Akita H. Tetrahedron Lett. 38 (1997) 1805
24. Kato K., Ono M., and Akita H. Tetrahedron: Asymm. 8 (1997) 2295
25. Kato K., Ono M., and Akita H. Tetrahedron 57 (2001) 10055
26. For a review concerning biological activity and syntheses, see ref. 25 and references cited therein.
27. Chen C.-S., and Sih C.J. Angew. Chem.. Int. Ed. Engl. 28 (1989) 695
28. Akaike H., Horie H., Kato K., and Akita H. Tetrahedron: Asymm. 19 (2008) 1100
29. Argoudelis A.D., and Zieserl J.Z. Tetrhedron Lett. (1966) 1969
30. Fukuyama K., Katsube Y., Noda A., Hamasaki T., and Hatsuda Y. Bull. Chem. Soc. Jpn. 51 (1978) 3175
31. Valverde S., Herradon B., Rabanal R.M., and Martin-Lomas M. Can. J. Chem. 65 (1986) 339
32. Hiraoka H., Furuta K., Ikeda K.N., and Yamamoto H. Bull. Chem. Soc. Jpn. 57 (1984) 2777
33. Murayama T., Sugiyama T., and Yamashita K. Agric. Biol. Chem. 51 (1987) 2055
34. Schlessinger R.H., and Gillman K.W. Tetrahedron Lett. 40 (1999) 1257
35. Ramesh S., and Franck R.W. Tetrahedron: Asymm. 1 (1990) 137
36. Masaki Y., Imaeda T., Oda H., Itoh A., and Shiro M. Chem. Lett. (1992) 1209
37. Shing T.K.M., and Aloui M. Can. J. Chem. 68 (1990) 1035
38. Gomez A.M., Valverde S., and Lopez J. Chem. Commum. (1997) 1647
39. Honda T., Sano N., and Kanai K. Heterocycles 41 (1995) 425
40. Yang Z.-C., and Zhou W.-S. Tetrahedron Lett. 36 (1995) 5617
41. Honda T., Mizutani H., and Kanai K. J. Chem. Soc. Perkin Trans. 1 (1996) 1729
42. Yang Z.-C., Wang Z.-W., and Zhou W.-S. J. Chem. Soc. Perkin Trans. 1 (1997) 317
43. Kanai K., Sano N., and Honda T. Heterocycles 50 (1999) 433
44. Lombardo M., Girotti R., Morganti S., and Trombini C. Org. Lett. 3 (2001) 2981
45. In: Grubbs R.H. (Ed). Handbook of Metathesis (2003), WILEY-VCH
46. Lombardo M., Gianotti K., Licciulli S., and Trombini C. Tetrahedron 60 (2004) 11725
47. Scholl M., Ding S., Lee C.W., and Grubbs R.H. Org. Lett. 1 (1999) 953
48. Lombardo M., Morganti S., and Trombini C. J. Org. Chem. 68 (2003) 997
49. Paquette L.A., and Mitzel T.M. J. Am. Chem. Soc. 118 (1996) 1931
50. Sutou N., Kato K., and Akita H. Tetrahedron: Asymm. 19 (2008) 1833
51. Rao K.V. Antibiot. Chemother. 10 (1960) 312
52. Marsh W.S., Garretson A.L., and Wesel E.M. Antibiot. Chemother. 10 (1960) 316
53. Werner R.F., and Demain A. J. Antibiot. 34 (1981) 551
54. Kanamaru T., Nakano Y., Toyoda Y., Miyagawa K., Tada M., Kaisho T., and Nakao M. Antimicrob. Agents Chemother. 45 (2001) 2455
55. Dirlam J.P., Clark D.A., and Hecker S.J. J. Org. Chem. 51 (1986) 4920
56. Shue Y.-K. Tetrahedron Lett. 37 (1996) 6447
57. Takeda T., and Mukaiyama T. Chem. Lett. (1980) 163
58. Preobrazhenskaya M.N., Balashova E.G., Turchin K.F., Padeiskaya E.N., Yvarova N.V., Pershin G.N., and Suvorov M.N. Tetrahedron Lett. 24 (1968) 6131
59. Hasuoka A., Nakayama Y., Adachi M., Kamiguchi H., and Kamiyama K. Chem. Pharm. Bull. 49 (2001) 1604
60. Larock R.C., and Yum E.K. J. Am. Chem. Soc. 113 (1991) 6689
61. Akita H., Sutou N., Sasaki T., and Kato K. Tetrahedron 62 (2006) 11592
62. Deborah L.M., Marcin D., Teresa K.-C., Nadya I.T., and Christopher J.M. Bioorg. Med. Chem. Lett. 17 (2007) 2380
63. Bando T., and Shishido K. Heterocycles 46 (1997) 111
64. Ojika M., Suzuki Y., Tsukamoto A., Sakagami Y., Fudou R., Yoshimura T., and Yamanaka S. J. Antibiot. 51 (1998) 275
65. Suzuki Y., Ojika M., Sakagami Y., Fudou R., and Yamanaka S. Tetrahedron 54 (1998) 11399
66. Gerth K., Irschik H., Reichenbach H., and Trowitzsch W. J. Antibiot. 33 (1980) 1474
67. Böhlendrof B., Herrmann M., Hecht H.-J., Sasse F., Forche E., Kunze B., Reichenbach H., and Höfle G. Eur. J. Org. Chem. (1999) 2601
68. Kato K., Nishimura A., Yamamoto Y., and Akita H. Tetrahedron Lett. 43 (2002) 643
69. Kato K., Sasaki T., Takayama H., and Akita H. Tetrahedron 59 (2003) 2679
70. Martin B.J., Clough J.M., Pattenden G., and Waldron I.R. Tetrahedron Lett. 34 (1993) 5151
71. Backhaus D. Tetrahedron Lett. 41 (2000) 2087
72. Williams D.R., Patnaik S., and Clark M.P. J. Org. Chem. 66 (2001) 8463
73. Söker U., Sasse F., Forche E., Kunze B., and Höfle G. Eur. J. Org. Chem. (2000) 1497
74. Bach T., and Heuser S. Chem Eur. J. 8 (2002) 5585
75. DeRoy P.L., and Charette A.B. Org. Lett. 5 (2003) 4163
76. Ojika M., Watanabe T., Qi J J., Tanino T., and Sakagami Y. Tetrahedron 60 (2004) 187
77. Panek J.S., and Shao J. Org. Lett. 6 (2004) 3083
78. Gebauser J., Arseniyadis S., and Cossy J. Eur. J. Org. Chem. (2008) 2701
79. Bach T., and Heuser S. Angew. Chem. Int. Ed. 40 (2001) 3184
80. Kato K., Nishimura A., Yamamoto Y., and Akita H. Tetrahedron Lett. 42 (2001) 4203
81. Sasaki T., Kato K., and Akita H. Chem. Pharm. Bull. 52 (2004) 770
82. Akita H., Sasaki T., Takayama H., and Kato K. Heterocycles 66 (2005) 219
83. Akita H., Sasaki T., Kato K., Suzuki Y., Kondo K., Sakagami Y., Ojika M., Fudou R., and Yamanaka S. Tetrahedron 60 (2004) 4735
84. Takayama H., Kato K., and Akita H. Eur. J. Org. Chem. (2006) 644
85. Takayama H., Kato K., Kimura M., and Akita H. Heterocycles 71 (2007) 75
86. Blakemore P.R. J. Chem. Soc., Perkin Trans. 1 (2002) 2563
87. Tsuji J., Takahashi M., and Takahashi T. Tetrahedron Lett. 21 (1980) 849
88. Inanaga J., Baba Y., and Hanamoto T. Chem. Lett. (1993) 241
89. Rhoads S.J., Chattopadhyay J.K., and Waali E.E. J. Org. Chem. 35 (1970) 3352
90. Iwaki Y., Yamamura S., and Akita H. Tetrahedron: Asymm. 19 (2008) 2192
91. Suzuki Y., Ojika M., and Sakagami Y. Biosci. Biotecnol. Biochem. 68 (2004) 390
92. Chang G., Guida W.C., and Still W.C. J. Am. Chem. Soc 111 (1989) 4379
93. Saunders M., Houk K.N., and Wu Y.D. J. Am. Chem. Soc 112 (1990) 1419
94. Iwaki Y., and Akita H. Chem. Pharm. Bull 55 (2007) 1610
95. Akita H., Iwaki Y., Kato K., Qi J., and Ojika M. Tetrahedron: Asymm. 18 (2007) 513
96. Akita H., Nozawa M., and Nagumo S. Chem. Pharm. Bull. 42 (1994) 1208
97. Iwaki Y., Kaneko M., and Akita H. Tetrahedron Lett. 49 (2008) 7024
98. Iwaki Y., Kaneko M., and Akita H. Tetrahedron: Asymm. 20 (2009) 298
99. Steinmetz H., Forche E., Reichenbach H., and Höfle G. Tetrahedron 56 (2000) 1681
100. Thierbach G., and Reichenbach H. Biochim. Biophys. Acta 638 (1981) 282
101. Ahn J.-W., Woo S.-H., Lee C.-O., Cho K.-Y., and Kim B.-S. J. Nat. Prod. 62 (1999) 495
102. Trowitzsch W., Reifenstahl G., Wray V., and Gerth K. J. Antibiot. 33 (1980) 1480
103. Trowitzsch W., Höfle G., and Sheldrick W.S. Tetrahedron Lett. 22 (1981) 3829
104. Clough J.M., Dube H., Martin B.J., Pattenden K.S.G., Reddy I.R., and Waldron. Org. Biomol. Chem. 4 (2006) 2906