Stereocontrol between remote atom centers using chiral acetals and its application to asymmetric syntheses of natural products

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 67, Issue 6, 2009, Pages 606-617

  Fujioka, Hiromichi ^a   Kita, Yasuyuki ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b RITSUMEIKAN UNIVERSITY   (Japan)

Author keywords

(+) Sch 642305; Asymmetric synthesis; Diene acetal; Ene acetal; Intramolecular haloetherification; Rubrenolide; Rubrynolide; Scyphstatin

Indexed keywords

STEREOSELECTIVITY;

(+)-SCH 642305; ASYMMETRIC SYNTHESIS; DIENE ACETAL; ENE ACETAL; INTRAMOLECULAR HALOETHERIFICATION; RUBRENOLIDE; RUBRYNOLIDE; SCYPHSTATIN;

OLEFINS;

EID: 69749112442     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.67.606     Document Type: Review

References (70)

1. (a) T. W. Greene, P. G. M. Wuts, In "Protective Groups in Organic Synthesis" 3 rd ed., John Wiley & Sons, Inc., New York, 1999, p 297;
2. (b) J. R. Hanson, In "Protecting Groups in Organic Synthesis" 1 st ed., Blackwell Science, Inc., Maiden, MA 1999, p 37;
3. (c) P. J. Kocienski, "Protecting Groups" 1st ed., George Thieme Verlag, Stuttgart, 1994, p 156
4. T. Mukaiyama, Organic Reactions, 28, 203 (1982)
5. (a) H. Yamamoto, A. Mori, J. Synth. Org. Chem., Jpn., 45, 944 (1987);
6. (b) E. A. Mash, Studies in Natural Products Chemistry, 1, 577 (1988);
7. (c) A Alexakis, P. Mangeny, Tetrahedron: Asymmetry, 1, 477 (1990);
8. (d) Y. Kita, H. Fujioka, Kikan Kagaku Sosetsu, 19, 157 (1993);
9. (e) H. Fujioka, Y. Kita, Studies in Natural Products Chemistry, 14, 469 (1994);
10. (f) H. Fujioka, The Fifth Series of Experimental Chemistry (Jikken Kagaku Kouza), 19 (VII), 210 (2004)
11. (a) H. Fujioka, Adv. Pharm. Scienc, 9, 149 (1993);
12. (b) H. Fujioka, idem, J. Pharm. Japan (Yakugaku Zasshi), 125, 699 (2005)
13. For acyclic stereocontrol between remote atom centers, see: K. Mikami, M. Shimizu, H.-C. Zhang, B. E. Maryanoff, Tetrahedron, 57, 2919 (2001)
14. (a) H. Fujioka, H. Kitagawa, N. Matsunaga, Y. Nagatomi, Y. Kita, Tetrahedron Lett., 37, 2245 (1996);
15. (b) H. Fujioka, H. Kitagawa, Y. Nagatomi, Y. Kita, J. Org. Chem., 61, 7309 (1996)
16. Z.-M. Wang, K. B. Sharpless, J. Org. Chem., 59, 8302 (1994)
17. M. D. Lewis, J. K. Cha, Y. Kishi, J. Am. Chem. Soc., 104, 4976 (1982)
18. (a) T-M. Yuan, S-M. Yeh, Y.-T. Hsieh, T.-Y. Luh, J. Org. Chem., 59, 8192 (1994);
19. (b) Y.-H. Chen, T.-Y. Luh, G.-H. Lee, S.-M. Peng, J. Chem. Soc., Chem. Commun., 1994, 2369
20. For asymmetric desymmetrization by chemical reaction, see: (a) K. Mikami, A, Yoshida, J. Synth. Org. Chem., Jpn., 60, 732 (2002);
21. (b) M. C. Willis, J. Chem. Soc., Perkin Trans. 1, 1999, 1765;
22. (c) S. R. Magnuson, Tetrahedron, 51, 2167 (1995);
23. (d) C. S. Poss, S. L. Schreiber, Acc. Chem. Res., 27, 9 (1994);
24. (e) R. S. Ward, Chem. Soc. Rev., 19, 1 (1990); For asymmetric desymmetrization by enzymatic reaction, see:
25. (f) C.R. Johnson, Acc. Chem. Res., 31, 333 (1998);
26. (g) E. Schoffers, A. Golebiowski, C. R. Johnson, Tetrahedron, 52, 3769 (1996);
27. (h) E. Santaniello, P. Ferraboschi, P. Grisenti, A. Manzocchi, Chem. Rev., 92, 1071 (1992);
28. M. Ohno, S. Kobayashi, M. Kurihara, J. Synth. Org. Chem., Jpn., 44, 38 (1986)
29. H. Fujioka, N. Kotoku, Y. Sawama, H. Kitagawa, Y. Ohba, T.-L. Wang, Y. Nagatomi, Y. Kita, Chem. Pharm. Bull., 53, 952(2005)
30. H. Fujioka, Y. Ohba, H. Hirose, K. Murai, Y. Kita, Angew. Chem. Int. Ed., 44, 734 (2005)
31. (a) Y. Kita, H. Namubu, N. G. Ramesh, G. Anilkumar, M. Matsugi, Org. Lett, 3, 1157 (2001);
32. (b) H. Namubu, G. Anilkumar, M. Matsugi, Y. Kita, Tetrahedron, 59, 77 (2003); For the radical reduction using VA-061 in water, see:
33. (c) H. Namubu, A. H. Alinejad, K. Hata, H. Fujioka, Y. Kita, Tetrahedron Lett., 45, 8927 (2004)
34. H. Fujioka, H. Kitagawa, M. Kondo, Y. Kita, Heterocycles, 37, 743 (1994)
35. (a) H. Fujioka, N. Kotoku, Y. Sawama, Y. Nagatomi, Y. Kita, Tetrahedron Lett., 43, 4825 (2002);
36. (b) H. Fujioka, Y. Sawama, N. Kotoku, T. Okitsu, T. Onaka, N. Murata, Y. Kita, Chem. Eur. J., 13, 10225 (2007)
37. For the structure determination of scyphostatin including the absolute configurations of cyclohexanone unit and biological activity, see: (a) M. Tanaka, F. Nara, K. Suzuki-Konagai, T. Hosoya, T. Ogita, J. Am. Chem. Soc., 119, 7871 (1997);
38. (b) F. Nara, M. Tanaka, T. Hosoya, K. Suzuki-Konagai, T. Ogita, J. Antibiot., 52, 525 (1999);
39. (c) F. Nara, M. Tanaka, S. Masuda-Inoue, Y. Yamamoto, H. Doi-Yoshioka, K. Suzuki-Konagai, S. Kumakura, T. Ogita, J. Antibiot., ibid., 52, 531 (1999);
40. For the determination of the absolute configurations of side chain, see: (d) S. Saito, N. Tanaka, K. Fujimoto, H. Kogen, Org. Lett., 2, 505 (2000)
41. (a) M. Inoue, W. Yokota, M. G. Murugesh, T. Izuhara, T. Katoh, Angew. Chem. Int. Ed., 43, 4207 (2004);
42. (b) M. Inoue, W. Yokota, T. Katoh, Synthesis, 2007, 622
43. R. Takagi, W. Miyanaga, K. Tojo, S. Tsuyumine, K. Ohkata, J. Org. Chem., 72, 4117 (2007)
44. (a) H. Fujioka, Y. Sawama, N. Murata, T. Okitsu, O. Kubo, S. Matsuda, Y. Kita, J. Am. Chem. Soc. 126, 11800 (2004);
45. (b) H. Fujioka, T. Okitsu, Y. Sawama, N. Murata, R. Li, Y. Kita, J. Am. Chem. Soc., ibid., 128, 5930 (2006)
46. T. R. Hoye, M. A Tennakoon, Org. Lett, 2, 1481 (2000)
47. H. Fujioka, Y. Ohba, K. Nakahara, M. Takatsuji, K. Murai, M. Ito, Y. Kita, Org. Lett., 9, 5605 (2007)
48. M. Chu, R. Mierzwa, L. Xu, L. He, J. Terracciano, M. Patel, V. Gullo, T. Black, W. Zhao, T.-M. Chan, A T. McPhail, J. Nat Prod., 66, 1527(2003)
49. S. K. Arya, C. Guo, S. F. Josephs, F. Wong-Staal, Science, 229, 69(1985)
50. (a) G. Mehta, H. M. Shinde, Chem. Commun., 2005, 3703;
51. (b) B. B. Snider, J. Zhou, Org. Lett, 8, 1283 (2006);
52. (c) K. Ishigami, R. Katsuta, H. Watanabe, Tetrahedron, 62, 2224 (2006);
53. (d) E. M. Wilson, D. Trauner, Org. Lett, 9, 1327 (2007)
54. E. J. Corey, K. C. Nicolaou, J. Am. Chem. Soc., 96, 5614 (1974)
55. Y. Ohba, M. Takatsuji, K. Nakahara, H. Fujioka, Y. Kita, Chem. Eur. J., in press
56. For isolation and structure elucidation, see: (a) N. C Franca, O. R. Gottlieb, D. T. Coxon, W. T. Ollis, Anais Acad. Brasil. Cienc, 43, 123 (1971);
57. (b) N. C. Franca, O. R. Gottlieb, D. T. Coxon, W. D. Ollis, J. Chem. Soc., Chem. Commun., 9, 514 (1972);
58. (c) N. C Franca, O. R. Gottlieb, D. T. Coxon, Phytochemistry, 16, 257 (1977);
59. For a review, see: (d) R. O. Gottlieb, B. W. Mors, J. Agrie Food Chem., 28, 196 (1980);
60. Although wrong stereochemical structures of rubrenolide and rubrynolide were originally proposed, the correct ones were reported by B. Zwanenburg et al. (rubrenolide : réf. 27a) and by S. K. Tayor et al. (rubrynolide : ref. 32c)
61. For asymmetric total synthesis of rubrenolide, see : (a) T. Saito, L. Thijs, J.-G. Ettema, B. Zwanenburg, Tetrahedron Lett., 34, 3589 (1993);
62. (b) L. Thijs, B. Zwanenburg, Tetrahedron, 60, 5237 (2004);
63. For the total synthesis of (±)-rubrynolide synthesis, see : (c) S. K. Taylor, J. A. Hopkins, K. A. Spangenberg, J. Org. Chem., 56, 5951 (1991)
64. (a) H. Fujioka, Y. Ohba, H. Hirose, K. Murai, Y. Kita, Org. Lett., 7, 3303 (2005);
65. (b) H. Fujioka, H. Hirose, Y. Ohba, K. Murai, K. Nakahara, Y. Kita, Tetrahedron, 63, 638 (2007)
66. (a) H. Fujioka, Y. Nagatomi, H. Kitagawa, Y. Kita, J. Am. Chem. Soc., 119, 12016 (1997);
67. (b) H. Fujioka, Y. Nagatomi, N. Kotoku, H. Kitagawa, Y. Kita, Tetrahedron, 56, 10141 (2000);
68. (c) H. Fujioka, N. Kotoku, Y. Nagatomi, Y. Kita, Tetrahedron Lett., 41, 1829 (2000);
69. (d) H. Fujioka, T. Fujita, N. Kotoku, Y. Ohba, A Hiramatsu, Y. Kita, Chem. Eur. J., 10, 5386 (2004)
70. H. Fujioka, K. Murai, Y. Ohba, H. Hirose, Y. Kita, Chem. Commun., 2006, 832