Enantioselective total synthesis of biologically active natural products using proline-catalyzed asymmetric aldol reactions

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 67, Issue 1, 2009, Pages 65-75

  Komatsu, Yoshiyuki ^a   Ikishima, Hideaki ^a   Okuyama, Atsushi ^a   Nakamura, Mutsumi ^a   Kotsuki, Hiyoshizo ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

(+) boronolide; (+) prosophylline; (5R,6S) ( ) 6 acetoxy 5 hexadecanolide; D ribo C 18 phytosphin Gosine; Enantioselective natural product synthesis; Organocatalytic asymmetric aldol; Pachastrissamine; Proline

Indexed keywords

ALDEHYDES; CATALYSIS; CHEMICAL REACTIONS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; SELECTIVE CATALYTIC REDUCTION;

(+) -BORONOLIDE; (+)-PROSOPHYLLINE; (5R,6S)-(-)-6-ACETOXY-5-HEXADECANOLIDE; NATURAL PRODUCT SYNTHESIS; ORGANOCATALYTIC; PACHASTRISSAMINE; PROLINE;

KETONES;

EID: 63049133072     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.67.65     Document Type: Article

References (78)

1. (a) U. Eder, G. Sauer, R. Wiechert, Angew. Chem., Int. Ed. Engl, 10, 496 (1971);
2. (b) Z. G. Hajos, D. R. Parrish, J. Org. Chem., 39, 1615 (1974)
3. Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem., Int. Ed. Engl., 36, 1871 (1997)
4. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc., 122, 2395 (2000)
5. C.-H. Wong, G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamon: Oxford, 1994
6. (a) A. Berkessel, H. Gröger, eds., Asymmetrie Organocatalysis, Wiley-VCH: Weinheim, 2005;
7. (b) P. I. Daiko, ed., Enantioselective Organocatalysis, Wiley-VCH: Weinheim, 2007
8. Japanese source
9. (b) Y. Hayashi, J. Synth. Org. Chem., Jpn., 63, 464 (2005);
10. (c) F. Tanaka, C. F. Barbas III, ibid., 63, 709 (2005);
11. Japanese source
12. Japanese source
13. (f) S. Saito, N. Momiyama, H. Yamamoto, J. Synth. Org. Chem., Jpn., 66, 774 (2008)
14. (a) H. Kotsuki, H. Ikishima, A. Okuyama, Heterocycles, 75, 493 (2008);
15. (b) idem, ibid., 75, 757 (2008)
16. S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc., 125, 2475 (2003)
17. (a) B. List, P. Pojarliev, C. Castello, Org. Lett., 3, 573 (2001);
18. (b) B. List, Synlett, 2001, 1675
19. B. Sun, L. Peng, X. Chen, Y. Li, Y. Li, K. Yamasaki, Tetrahedron: Asymmetry, 16, 1305 (2005)
20. Y. Sekiguchi, A. Sasaoka, A. Shimomoto, S. Fujioka, H. Kotsuki, Synlett, 2003, 1655
21. M. Yus, C. Nájera, F. Foubelo, Tetrahedron, 59, 6147 (2003)
22. H. Ikishima, Y. Sekiguchi, Y. Ichikawa, H. Kotsuki, Tetrahedron, 62, 311 (2006)
23. B. R. Laurence, J. A. Pickett, J. Chem. Soc., Chem. Commun., 1982, 59
24. (a) H. Kotsuki, I. Kadota, M. Ochi, J. Org. Chem., 55, 4417 (1990);
25. (b) H. Kotsuki, J. Synth. Org. Chem., Jpn., 57, 334 (1999)
26. J. F. Anderson, T. G. Andreadis, C. R. Vossbrinck, S. Tirrell, E. M. Wakem, R. A. French, A. E. Garmendia, H. J. V. Kruiningen, Science, 286, 2331 (1999)
27. S. G. Hegde, Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, ed., Wiley: New York, 1995; Vol. 4, p 2381
28. (a) H. Ikishima, A. Okuyama, T. Ishii, Y. Ichinohe, H. Kotsuki, 21st ICHC QuIy 15, 2007);
29. Japanese source
30. N. C. Franca, J. Polonsky, C. R. Acad. Sci., Ser. C, 273, 439 (1971)
31. A. Kjaer, R. Norrestam, J. Polonsky, Acta Chem. Scand., Ser. B, 39, 745 (1985)
32. (a) C. W. Jefford, M. C. Moulin, Helv. Chim. Acta, 74, 336 (1991);
33. (b) H. Nagano, H. Yasui, Chem. Lett., 1992, 1045;
34. (c) T. Honda, S. Horiuchi, H. Mizutani, K. Kanai, J. Org. Chem., 61, 4944 (1996);
35. (d) A. K. Ghosh, G. Bilcer, Tetrahedron Lett., 41, 1003 (2000);
36. (e) M. Chandrasekhar, S. Raina, V. K. Singh, ibid., 41, 4969 (2000);
37. (f) M. Carda, S. Rodriguez, B. Segovia, J. A. Marco, J. Org. Chem., 67, 6560 (2002);
38. (g) B. M. Trost, V. S. C. Yeh, Org. Lett., 20, 3513 (2002);
39. (h) M. Chandrasekhar, K. L. Chandra, V. K. Singh, J. Org. Chem., 68, 4039 (2003);
40. (i) S.-G. Hu, T.-S. Hu, Y.-L. Wu, Org. Biomol. Chem., 2, 2305 (2004);
41. (j) S. V. Naidu, P. Gupta, P. Kumar, Tetrahedron Lett., 46, 2129 (2005);
42. (k) P. Kumar, S. V. Naidu, J. Org. Chem., 71, 3935 (2006);
43. (l) K. R. Prasad, P. Anbarasan, Tetrahedron: Asymmetry, 17, 1146 (2006);
44. S. Raghavan, V. Knshnaiah, Tetrahedron Lett., 47, 7611 (2006)
45. (a) M. Malinowska, P. Kwiatkowski, J. Jurczak, Tetrahedron Lett., 45, 7693 (2004);
46. (b) H. Kotsuki, K. Kumamoto, J. Synth. Org. Chem., Jpn., 63, 770 (2005)
47. D. Enders, M. Voith, A. Lenzen, Angew. Chem. Int. Ed., 44, 1304 (2005)
48. K.-M. Chen, K. G. Gunderson, G. E. Hardtmann, K. Prasad, O. Repic, M. J. Shapiro, Chem. Lett., 1987, 1923
49. O. Mitsunobu, Synthesis, 1981, 1
50. Y. Torisawa, H. Okabe, S. Ikegami, Chem. Lett., 1984, 1555
51. B. Czakó, L. Kürti, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier: Amsterdam, 2005, p 346
52. Japanese source
53. J. Zellner, Monatsh. Chem., 32, 133 (1911)
54. O. Shirota, K. Nakanishi, N. Berova, Tetrahedron, 55, 13643 (1999)
55. (a) M. Morita, K. Motoki, K. Akimoto, T. Natori, T. Sakai, E. Sawa, K. Yamaji, Y. Koezuka, E. Kobayashi, H. Fukushima, J. Med. Chem., 38, 2176 (1995);
56. (b) T. Kawano, J. Cui, Y. Koezuka, I. Toura, Y. Kaneko, K. Motoki, H. Ueno, R. Nakagawa, H. Sato, E. Kondo, H. Koseki, M. Taniguchi, Science, 278, 1626 (1997)
57. A. R. Howell, R. C. So, S. K. Richardson, Tetrahedron, 60, 11327 (2004).
58. S. Kim, N. Lee, S. Lee, T. Lee, Y. M. Lee, J. Org. Chem., 73, 1379 (2008)
59. D. Enders, J. Paleček, C. Grondai, Chem. Commun., 2006, 655
60. I. Kuroda, M. Musman, I. I. Ohtani, T. Ichiba, J. Tanaka, D. G. Grávalos, T. Higa, J. Nat. Prod., 65, 1505 (2002)
61. V. Ledroit, C. Debitus, C. Lavaud, G. Massiot, Tetrahedron Lett., 44, 225 (2003)
62. E. Abraham, S. G. Davies, P. M. Roberts, A. J. Russell, J. E. Thomson, Tetrahedron: Asymmetry, 19, 1027 (2008)
63. J. Y. Ichikawa, K. Matsunaga, T. Masuda, H. Kotsuki, K. Nakano, Tetrahedron, 64, 11313 (2008)
64. N. Sudhakar, A. R. Kumar, A. Prabhakar, B. Jagadeesh, B. V. Rao, Tetrahedron Lett., 46, 325 (2005)
65. D. Enders, V. Terteryan, J. Paleček, Synthesis, 2008, 2278
66. T. Lee, S. Lee, Y. S. Kwak, D. Kim, S. Kim, Org. Lett., 9, 429 (2007)
67. (a) G. Ratle, X. Monseur, B. C. Das, J. Yassi, Q. Khuong-Huu, R. Goutarel, Bull. Soc. Chim. Fr., 1966, 2945;
68. (b) Q. Khuong-Huu, G. Ratle, X. Monseur, R. Goutarel, Bull. Soc. Chim. Belg., 81,443 (1972)
69. (a) C. Agami, F. Couty, H. Mathieu, Tetrahedron Lett., 39, 3505 (1998);
70. (b) I. Kadota, M. Kawada, Y. Muramatsu, Y. Yamamoto, Tetrahedron: Asymmetry, 8, 3887 (1997);
71. (c) A. Datta, J. S. R. Kumar, S. Roy, Tetrahedron, 57, 1169 (2001);
72. (d) Q. Wang, N. A. Sakaki, J. Org. Chem., 69, 4767 (2004);
73. (e) S. D. Koulocheri, S. A. Haroutounian, Tetrahedron Lett., 40, 6869 (1999);
74. (f) C. Herdeis, J. Telser, Eur. J. Org. Chem., 1999, 1407;
75. (g) C. Yang, L. Liao, Y. Xu, H. Zhang, P. Xia, W. Zhou, Tetrahedron: Asymmetry, 10, 2311 (1999)
76. J. Cossy, C. Willis, V. Bellosta, S. BouzBouz, J. Org. Chem., 67, 1982 (2002)
77. G. Stork, K. Zhao, Tetrahedron Lett., 30, 287 (1989)
78. N. Toyooka, Y. Yoshida, Y. Yotsui, T. Momose, J. Org. Chem., 64, 4914 (1999)