Enantioselective total synthesis of octalactin a using asymmetric aldol reactions and a rapid lactonization to form a medium-sized ring

Chemistry - A European Journal

Volumn 11, Issue 22, 2005, Pages 6601-6608

  Shiina, Isamu ^a   Hashizume, Minako ^a   Yamai, Yu Suke ^a   Oshiumi, Hiromi ^a   Shimazaki, Takahisa ^a   Takasuna, Yu Ji ^a   Ibuka, Ryoutarou ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Aldol reaction; Enantioselectivity; Octalactin A; Rapid lactonization; Total synthesis

Indexed keywords

ALCOHOLS; CATALYSIS; SYNTHESIS (CHEMICAL); TUMORS;

ALDOL REACTIONS; ENANTIOSELECTIVITY; OCTALACTIN A; RAPID LACTONIZATION; TOTAL SYNTHESIS;

ORGANIC COMPOUNDS;

ANTINEOPLASTIC AGENT; CEPHALOSPOROLIDE D; LACTONE; OCTALACTIN A; OCTALACTIN B;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; LACTONES; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 27744480366     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500417     Document Type: Article

References (74)

1. D. M. Tapiolas, M. Roman, W. Fenical, T. J. Stout, J. Clardy, J. Am. Chem. Soc. 1991, 113, 4682-4683.
2. R. D. Norcross, I. Paterson, Chem. Rev. 1995, 95, 2041-2114.
3. K. R. Buszek, N. Sato, Y. Jeong, J. Am. Chem. Soc. 1994, 116, 5511-5512.
4. J. C. McWilliams, J. Clardy, J. Am. Chem. Soc. 1994, 116, 8378-8379.
5. K. R. Buszek, N. Sato, Y. Jeong, Tetrahedron Lett. 2002, 43, 181-184.
6. P. T. O'Sullivan, W. Buhr, M. A. M. Fuhry, J. R. Harrison, J. E. Davies, N. Feeder, D. R. Marshall, J. W. Burton, A. B. Holmes, J. Am. Chem. Soc. 2004, 126, 2194-2207.
7. Partial syntheses: a) K. R. Buszek, Y. Jeong, Tetrahedron Lett. 1995, 36, 7189-7192;
8. b) M. B. Andrus, A. B. Argade, Tetrahedron Lett. 1996, 37, 5049-5052;
9. c) M. Kodama, M. Matsushita, Y. Terada, A. Takeuchi, S. Yoshio, Y. Fukuyama, Chem. Lett. 1997, 117-118;
10. d) S. Inoue, Y. Iwabuchi, H. Irie, S. Hatakeyama, Synlett 1998, 735-736;
11. e) J. Bach, J. Garcia, Tetrahedron Lett. 1998, 39, 6761-6764;
12. f) other synthetic studies: J. Bach, R. Berenguer, J. Garcia, J. Vilarrasa, Tetrahedron Lett. 1995, 36, 3425-3428;
13. g) A. N. Hulme, G. E. Howells, Tetrahedron Lett. 1997, 38, 8245-8248;
14. h) F. Shimoma, H. Kusaka, K. Wada, H. Azami, M. Yasunami, T. Suzuki, H. Hagiwara, M. Ando, J. Org. Chem. 1998, 63, 920-929;
15. i) J. R. Harrison, A. B. Holmes, I. Collins, Synlett 1999, 972-974;
16. j) E. A. Anderson, A. B. Holmes, I. Collins, Tetrahedron Lett. 2000, 41, 117-121;
17. k) G. Bluet, J.-M. Campagne, Synlett 2000, 221-222.
18. a) I. Shiina, Y. Fukuda, T. Ishii, H. Fujisawa, T. Mukaiyama, Chem. Lett. 1998, 831-832;
19. b) I. Shiina, H. Fujisawa, T. Ishii, Y. Fukuda, Heterocycles 2000, 52, 1105-1123.
20. a) T. Mukaiyama, S. Kobayashi, H. Uchiro, I. Shiina, Chem. Lett. 1990, 129-132;
21. b) S. Kobayashi, H. Uchiro, Y. Fujishita, I. Shiina, T. Mukaiyama, J. Am. Chem. Soc. 1991, 113, 4247-4252;
22. c) S. Kobayashi, M. Furuya, A. Ohtsubo, T. Mukaiyama, Tetrahedron: Asymmetry 1991, 2, 635-638;
23. d) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772;
24. e) see also: T. Mukaiyama, H. Uchiro, I. Shiina, S. Kobayashi, Chem. Lett. 1990, 1019-1022;
25. f) T. Mukaiyama, I. Shiina, S. Kobayashi, Chem. Lett. 1991, 1901-1904;
26. g) S. Kobayashi, I. Shiina, J. Izumi, T. Mukaiyama, Chem. Lett. 1992, 373-376;
27. h) T. Mukaiyama, I. Shiina, J. Izumi, S. Kobayashi, Heterocycles 1993, 35, 719-724;
28. i) T. Mukaiyama, I. Shiina, H. Uchiro, S. Kobayashi, Bull. Chem. Soc. Jpn. 1994, 67, 1708-1716;
29. j) I. Shiina, R. Ibuka, Tetrahedron Lett. 2001, 42, 6303-6306.
30. I. Shiina in Modern Aldol Reactions (Eds.: R. Mahrwald), Wiley-VCH, Weinheim, 2004, pp. 105-165.
31. a) I. Shiina, S. Miyoshi, M. Miyashita, T. Mukaiyama, Chem. Lett. 1994, 515-518;
32. b) I. Shiina, T. Mukaiyama, Chem. Lett. 1994, 677-680;
33. c) see also: K. Ishihara, M. Kubota, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 4473-4414; corrigendum 6639;
34. d) K. Ishihara, M. Kubota, H. Kurihara, H. Yamamoto, J. Org. Chem. 1996, 61, 4560-4567.
35. I. Shiina, Tetrahedron 2004, 60, 1587-1599.
36. a) I. Shiina, H. Iwadare, H. Sakoh, M. Hasegawa, Y. Tani, T. Mukaiyama, Chem. Lett. 1998, 1-2;
37. b) I. Shiina, K. Saitoh, I. Fréchard-Ortuno, T. Mukaiyama, Chem. Lett. 1998, 3-4;
38. c) T. Mukaiyama, I. Shiina, H. Iwadare, M. Saitoh, T. Nishimura, N. Ohkawa, H. Sakoh, K. Nishimura, Y. Tani, M. Hasegawa, K. Yamada, K. Saitoh, Chem. Eur. J. 1999, 5, 121-161.
39. Preliminarily communication for the total synthesis of octalactin B: I. Shiina, H. Oshiumi, M. Hashizume, Y. Yamai, R. Ibuka, Tetrahedron Lett. 2004, 45, 543-547.
40. a) I. Shiina, R. Ibuka, M. Kubota, Chem. Lett. 2002, 286-287;
41. b) I. Shiina, M. Kubota, R. Ibuka, Tetrahedron Lett. 2002, 43, 7535-7539;
42. c) I. Shiina, M. Kubota, H. Oshiumi, M. Hashizume, J. Org. Chem. 2004, 69, 1822-1830;
43. d) I. Shiina, Yuki Gosei Kagaku Kyokaishi 2005, 62, 2-17;
44. e) see also: I. Shiina, Y. Kawakita, Tetrahedron 2004, 60, 4729-4733;
45. f) J. Tian, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Org. Lett. 2003, 5, 3021-3024;
46. g) M. Inoue, T. Sasaki, S. Hatano, M. Hirama, Angew. Chem. 2004, 116, 6662-6667;
47. Angew. Chem. Int. Ed. 2004, 43, 6500-6505.
48. a) Y. Guindon, A.-M. Faucher, É. Bourque, V. Caron, G. Jung, S. R. Landry, J. Org. Chem. 1997, 62, 9276-9283;
49. b) Y. Guindon, G. Jung, B. Guérin, W. W. Ogilvie, Synlett 1998, 213-220;
50. c) Y. Guindon, M. Bencheqroun, A. Bouzide, J. Am. Chem. Soc. 2005, 127, 554-558, and references therein.
51. a) S. Kiyooka, K. A. Shahid, F. Goto, M. Okazaki, Y. Shuto, J. Org. Chem. 2003, 68, 7967-7978;
52. b) S. Kiyooka, Tetrahedron: Asymmetry 2003, 14, 2897-2910, and references therein.
53. a) T. Mukaiyama, J. Matsuo, D. lida, H. Kitagawa, Chem. Lett. 2001, 846-847;
54. b) J. Matsuo, D. Iida, H. Yamanaka, T. Mukaiyama, Tetrahedron 2003, 59, 6739-6750.
55. a) J. Aebi, M. A. Sutter, D. Wasmuth, D. Seebach, Liebigs Ann. Chem. 1983, 2114-2126;
56. b) D. Seebach, J. Aebi, D. Wasmuth, Org. Synth. 1985, 63, 109-120;
57. c) D. Seebach, J. Aebi, D. Wasmuth, Org. Synth. Collect. 1990, 7, 153-159.
58. K. Mochizuki, K. Ohmori, H. Tamura, Y. Shizuri, S. Nishiyama, E. Miyoshi, S. Yamamura, Bull. Chem. Soc. Jpn. 1993, 66, 3041-3046.
59. a) Y. Guindon, Z. Liu, G. Jung, J. Am. Chem. Soc. 1997, 119, 9289-9290;
60. b) J.-P. Bouvier, G. Jung, Z. Liu, B. Guérin, Y. Guindon, Org. Lett. 2001, 3, 1391-1394;
61. c) Y. Guindon, K. Houde, M. Prévost, B. Cardinal-David, S. R. Landry, B. Daoust, M. Bencheqroun, B. Guérin, J. Am. Chem. Soc. 2001, 123, 8496-8501;
62. d) Y. Guindon, M. Prévost, P. Mochirian, B. Guérin, Org. Lett. 2002, 4, 1019-1022;
63. e) P. Mochirian, B. Cardinal-David, B. Guérin, M. Prévost, Y. Guindon, Tetrahedron Lett. 2002, 43, 7067-7071.
64. The ee of syn-41 was determined after its conversion to the corresponding lactone as shown in the Supporting Information.
65. M. Zhao, J. Li, E. Mano, Z. Song, D. M. Tschaen, E. J. J. Grabowski, P. J. Reider, J. Org. Chem. 1999, 64, 2564-2566.
66. H. Sajiki, K. Hirota, Tetrahedron 1998, 54, 13981-13996.
67. K. R. Buszek, Y. Jeong, N. Sato, P. C. Still, P. L. Muino, I. Ghosh, Synth. Commun. 2001, 31, 1781-1791.
68. Original 5-pyridyl ester methods for the synthesis of macrolactones: a) E. J. Corey, K. C. Nicolaou, J. Am. Chem. Soc. 1974, 96, 5614-5616;
69. b) H. Gerlach, A. Thalmann, Helv. Chim. Acta 1974, 57, 2661-2663;
70. c) E. J. Corey, D. J. Brunelle, Tetrahedron Lett. 1976, 17, 3409-3412;
71. d) see also the synthesis of unsaturated eight-membered lactones using the S-pyridyl ester method: K. C. Nicolaou, D. G. McGarry, P. K. Somers, B. H. Kim, W. W. Ogilvie, G. Yiannikouros, C. V. C. Prasad, C. A. Veale, R. R. Hark, J. Am. Chem. Soc. 1990, 112, 6263-6276.
72. T. Fukuyama, S.-C. Lin, L.-P. Li, J. Am. Chem. Soc. 1990, 112, 7050-7051.
73. [4] [α] = + 132° (enantiomorph).
74. [4] [α] = + 141° (enantiomorph).