Total synthesis of 10-isocyano-4-cadinene and its stereoisomers and evaluations of antifouling activities

Journal of Organic Chemistry

Volumn 76, Issue 16, 2011, Pages 6558-6573

  Nishikawa, Keisuke ^a   Nakahara, Hiroshi ^a   Shirokura, Yousuke ^a   Nogata, Yasuyuki ^b   Yoshimura, Erina ^c   Umezawa, Taiki ^a   Okino, Tatsufumi ^a   Matsuda, Fuyuhiko ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b CENTRAL RESEARCH INSTITUTE OF ELECTRIC POWER INDUSTRY   (Japan)

^c CERES Inc   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; ABSOLUTE STEREOCHEMISTRY; ANTIFOULING ACTIVITY; ANTIFOULING AGENTS; BALANUS AMPHITRITE; ENANTIOSELECTIVE TOTAL SYNTHESIS; INTERMOLECULAR DIELS-ALDER REACTIONS; SAMARIUM DIIODIDE; SESQUITERPENES; SYNTHETIC PATHWAYS; TOTAL SYNTHESIS;

CYCLIZATION; OPTICAL ROTATION; SAMARIUM; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ESSENTIAL OILS;

10 ISOCYANO 4 CADINENE; ANTIFOULING AGENT; SAMARIUM DIIODIDE; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; BARNACLE; CHEMICAL STRUCTURE; CYCLIZATION; DIELS ALDER REACTION; ENANTIOMER; NONHUMAN; REACTION ANALYSIS; STEREOISOMERISM; SYNTHESIS;

ANIMALS; CYANIDES; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; NAPHTHALENES; OPTICAL ROTATION; SESQUITERPENES; STEREOISOMERISM; THORACICA;

EID: 80051750552     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2008109     Document Type: Article

References (67)

1. Okino, T.; Yoshimura, E.; Hirota, H.; Fusetani, N. Tetrahedron 1996, 52, 9447-9454
2. Okino, T.; Yoshimura, E.; Hirota, H.; Fusetani, N. Tetrahedron Lett. 1995, 36, 8637-8640
3. Hirota, H.; Tomono, Y.; Fusetani, N. Tetrahedron 1996, 52, 2359-2368
4. Okino, T.; Yoshimura, E.; Hirota, H.; Fusetani, N. J. Nat. Prod. 1996, 59, 1081-1083
5. Clare, A. S. Biofouling 1996, 9, 211-229
6. Garson, M. J.; Simpson, J. S. Nat. Prod. Rep. 2004, 21, 164-179
7. Kitano, Y.; Ito, T.; Suzuki, T.; Nogata, Y.; Shinshima, K.; Yoshimura, E.; Chiba, K.; Tada, M.; Sakaguchi, I. J. Chem. Soc., Perkin Trans. 1 2002, 2251-2255
8. Kitano, Y.; Yokoyama, A.; Nogata, Y.; Shinshima, K.; Yoshimura, E.; Chiba, K.; Tada, M.; Sakaguchi, I. Biofouling 2003, 19, 187-192
9. Nogata, Y.; Kitano, Y.; Yoshimura, E.; Shinshima, K.; Sakaguchi, I. Biofouling 2004, 20, 87-91
10. Kitano, Y.; Nogata, Y.; Shinshima, K.; Yoshimura, E.; Chiba, K.; Tada, M.; Sakaguchi, I. Biofouling 2004, 20, 93-100
11. Evans, S. M. Biofouling 1999, 14, 117-129
12. Horiguchi, T.; Shiraishi, H.; Shimizu, M.; Yamazaki, S.; Morita, M. Mar. Pollut. Bull. 1995, 31, 402-405
13. Armstrong, E.; Boyd, K. G.; Burgess, J. G. Biotechnol. Annu. Rev. 2000, 6, 221-241
14. Negri, A. P.; Smith, D. S.; Webster, N. S.; Heyward, A. J. Mar. Pollut. Bull. 2002, 44, 111-117
15. Nishikawa, K.; Shirokura, Y.; Nakahara, H.; Nogata, Y.; Yoshimura, E.; Umezawa, T.; Okino, T.; Matsuda, F. Org. Lett. 2010, 12, 904-907
16. Vig, O. P.; Chugh, O. P.; Matta, K. L. Indian J. Chem. 1970, 8, 29-32
17. Kitahara, T.; Kurata, H.; Matsuoka, T.; Mori, K. Tetrahedron 1985, 41, 5475-5485
18. Vig, O. P.; Trehan, I. R.; Kumar, R. Indian J. Chem., Sect. B 1977, 15B, 319-321
19. Taber, D. F.; Gunn, B. P. J. Am. Chem. Soc. 1979, 101, 3992-3993
20. Parker, K. A.; Iqbal, T. J. Org. Chem. 1982, 47, 337-342
21. Katayama, M.; Marumo, S. Tetrahedron Lett. 1983, 24, 1703-1706
22. Vig, O. P.; Sharma, M. L.; Kiran, S.; Singh, J. Indian J. Chem., Sect. B 1983, 22B, 746-748
23. Mori, K.; Waku, M. Tetrahedron 1984, 40, 305-309
24. Parker, K. A.; Farmar, J. G. J. Org. Chem. 1986, 51, 4023-4028
25. Davidson, B. S.; Plavcan, K. A.; Meinwald, J. J. Org. Chem. 1990, 55, 3912-3917
26. Roush, W. R.; Champoux, J. A.; Peterson, B. C. Tetrahedron Lett. 1996, 37, 8989-8992
27. Tashiro, T.; Bando, M.; Mori, K. Synthesis 2000, 1852-1862
28. White, R. D.; Wood, J. L. Org. Lett. 2001, 3, 1825-1827
29. Miyaoka, H.; Shida, H.; Yamada, N.; Mitome, H.; Yamada, Y. Tetrahedron Lett. 2002, 43, 2227-2230
30. White, R. D.; Keaney, G. F.; Slown, C. D.; Wood, J. L. Org. Lett. 2004, 6, 1123-1126
31. Hodgson, D. M.; Foley, A. M.; Lovell, P. J. Synlett 1999, 744-746
32. Rüeger, H.; Stutz, S.; Spindler, F.; Maibaum, J. Tetrahedron Lett. 2000, 41, 10085-10089
33. Herbert, C. B.; Choi, Y. M.; Narasimhan, S. Inorg. Chem. 1981, 20, 4454-4456
34. Ukai, J.; Ikeda, Y.; Ikeda, N.; Yamamoto, H. Tetrahedron Lett. 1983, 24, 4029-4032
35. Tamura, R.; Saegusa, K.; Kakihana, M.; Oda, D. J. Org. Chem. 1988, 53, 2723-2728
36. Low, C. M. R. Synlett 1991, 123-124
37. Probst, M. F.; Modro, A. M.; Modro, T. A. Can. J. Chem. 1997, 75, 1131-1135
38. Cramer, C. J.; Harmate, M.; Rashataakhon, P. J. Org. Chem. 2001, 66, 5641-5644
39. Wang, Y.; West, F. G. Synthesis 2002, 99-103
40. Dureault, A.; Tranchepain, I.; Depezay, J. C. Synthesis 1987, 491-493
41. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 20, 399-402
42. Freire, F.; Seco, J. M.; Quiñoá, E.; Riguera, R. Chem.-Eur. J. 2005, 11, 5509-5522
43. Yoshida, K.; Grieco, P. A. J. Org. Chem. 1984, 49, 5257-5260
44. Grieco, P. A.; Galatsis, P.; Spohn, R. F. Tetrahedron 1986, 42, 2847-2853
45. Grieco, P. A.; Larsen, S. D.; Fobare, W. F. Tetrahedron Lett. 1986, 27, 1975-1978
46. Roush, W. R.; Barda, D. A. J. Am. Chem. Soc. 1997, 119, 7402-7403
47. Schürer, S. C.; Blechert, S. Synlett 1999, 1879-1882
48. Roush, W. R.; Limberakis, C.; Kunz, R. K.; Barda, D. A. Org. Lett. 2002, 4, 1543-1546
49. Halvorsen, G. T.; Roush, W. R. Org. Lett. 2007, 9, 2243-2246
50. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156
51. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287
52. Molander, G. A.; McKie, J. A. J. Org. Chem. 1993, 58, 7216-7227
53. Molander, G. A.; Harris, C. R. J. Org. Chem. 1997, 62, 2944-2956
54. Tamiya, H.; Goto, K.; Matsuda, F. Org. Lett. 2004, 6, 545-549
55. Oldenziel, O. H.; van Leusen, A. M. Tetrahedron Lett. 1973, 14, 1357-1360
56. Ireland, R. E.; Mander, L. N. J. Org. Chem. 1967, 32, 689-696
57. Ireland, R. E.; Mander, L. N. J. Org. Chem. 1969, 34, 142-152
58. Vishnumuthy, K.; Cheung, E.; Scheffer, J. R.; Scott, C. Org. Lett. 2002, 4, 1071-1074
59. Corey, E. J.; Myers, A. G. J. Am. Chem. Soc. 1985, 107, 5574-5576
60. Kuroda, C.; Kasahara, T.; Akiyama, K.; Amemiya, T.; Kunishima, T.; Kimura, Y. Tetrahedron 2002, 58, 4493-4504
61. Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Díaz, C. G. Synlett 2000, 1561-1564
62. Benneche, T.; Strande, P.; Undheim, K. Synthesis 1983, 762-763
63. Gómez, C.; Maciá, B.; Lillo, V. J.; Yus, M. Tetrahedron 2006, 62, 9832-9839
64. Miyaoka, H.; Yamanishi, M.; Kajiwara, Y.; Yamada, Y. J. Org. Chem. 2003, 68, 3476-3479
65. Shimazawa, R.; Suzuki, T.; Dodo, K.; Shirai, R. Bioorg. Med. Chem. Lett. 2004, 14, 3291-3294
66. Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021-3028
67. 13C NMR, MS) of the synthetic 35 were completely identical with those in the literature. Nogata, Y.; Yoshimura, E.; Shinshima, K.; Kitano, Y.; Sakaguchi, I. Biofouling 2003, 19, 193-196