Synthetic Studies on Biscembranoids. Asymmetric Total Synthesis of the 14-Membered Diene Unit of Methyl Sarcophytoate

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 6, 1998, Pages 1417-1429

  Yasuda, Minoru ^a   Ide, Mitsuaki ^a   Matsumoto, Yuka ^a   Nakata, Masaya ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000698904     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.1417     Document Type: Article

References (41)

1. T. Kusumi, M. Igari, M. O. Ishitsuka, A. Ichikawa, Y. Itezono, N. Nakayama, and H. Kakisawa, J. Org. Chem., 55, 6286 (1990).
2. S. Jingyu, L. Kanghou, P. Tangsheng, H. Cun-heng, and J. Clardy, J. Am. Chem. Soc., 108, 177 (1986).
3. S. Jingyu, L. Kanghou, P. Tangsheng, Z. Longmei, Z. Qitai, and L. Xiuyun, Scientia Sinica, Ser. B, 31, 1172 (1988).
4. P. A. Leone, B. F. Bowden, A. R. Carroll, J. C. Coll, and G. V. Meehan, J. Nat. Prod., 56, 521 (1993).
5. M. O. Ishitsuka, T. Kusumi, and H. Kakisawa, Tetrahedron Lett., 32, 2917 (1991).
6. M. O. Ishitsuka, T. Kusumi, and H. Kakisawa, Tetrahedron Lett., 32, 6595 (1991).
7. M. Nakata, M. Yasuda, S. Suzuki, and S. Ohba, Synlett, 1994, 71.
8. M. Yasuda, M. Ide, Y. Matsumoto, and M. Nakata, Synlett, 1997, 899.
9. a) M. Kodama, Y. Matsuki, and S. Ito, Tetrahedron Lett., 1975, 3065;
10. b) J.-F. Biellmann and J.-B. Ducep, Org. React., 27, 1 (1982);
11. c) J. A. Marshall and R. C. Andrews, J. Org. Chem., 50, 1602 (1985).
12. For the recent examples, see: a) C. Prandi and P. Venturello, J. Org. Chem., 59, 3494 (1994); b) K. Nakatani, A. Okamoto, M. Yamanuki, and I. Saito, J. Org. Chem., 59, 4360 (1994); c) M. Majewski, N. M. Irvine, and G. W. Bantle, J. Org. Chem., 59, 6697 (1994); d) R. D. Little, M. R. Masjedizadeh, O. Wallquist, and J. I. Mcloughlin, Org. React., 47, 315 (1995).
13. For the recent examples, see: a) C. Prandi and P. Venturello, J. Org. Chem., 59, 3494 (1994); b) K. Nakatani, A. Okamoto, M. Yamanuki, and I. Saito, J. Org. Chem., 59, 4360 (1994); c) M. Majewski, N. M. Irvine, and G. W. Bantle, J. Org. Chem., 59, 6697 (1994); d) R. D. Little, M. R. Masjedizadeh, O. Wallquist, and J. I. Mcloughlin, Org. React., 47, 315 (1995).
14. For the recent examples, see: a) C. Prandi and P. Venturello, J. Org. Chem., 59, 3494 (1994); b) K. Nakatani, A. Okamoto, M. Yamanuki, and I. Saito, J. Org. Chem., 59, 4360 (1994); c) M. Majewski, N. M. Irvine, and G. W. Bantle, J. Org. Chem., 59, 6697 (1994); d) R. D. Little, M. R. Masjedizadeh, O. Wallquist, and J. I. Mcloughlin, Org. React., 47, 315 (1995).
15. For the recent examples, see: a) C. Prandi and P. Venturello, J. Org. Chem., 59, 3494 (1994); b) K. Nakatani, A. Okamoto, M. Yamanuki, and I. Saito, J. Org. Chem., 59, 4360 (1994); c) M. Majewski, N. M. Irvine, and G. W. Bantle, J. Org. Chem., 59, 6697 (1994); d) R. D. Little, M. R. Masjedizadeh, O. Wallquist, and J. I. Mcloughlin, Org. React., 47, 315 (1995).
16. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, and K. B. Sharpless, J. Am. Chem. Soc., 109, 5765 (1987).
17. M. A. Umbreit and K. B. Sharpless, J. Am. Chem. Soc., 99, 5526 (1977).
18. The numbering system used for methyl sarcophytoate in Chemical Abstracts is employed in the discussion of all synthetic intermediates.
19. S. Murata, M. Suzuki, and R. Noyori, Bull. Chem. Soc. Jpn., 55, 247 (1982).
20. a) A. Yasuda, S. Tanaka, K. Oshima, H. Yamamoto, and H. Nozaki, J. Am. Chem. Soc., 96, 6513 (1974);
21. b) S. Tanaka, A. Yasuda, H. Yamamoto, and H. Nozaki, J. Am. Chem. Soc., 97, 3252 (1975);
22. c) A. Yasuda, H. Yamamoto, and H. Nozaki, Bull. Chem. Soc. Jpn., 52, 1705 (1979);
23. d) A. Yasuda, S. Tanaka, H. Yamamoto, and H. Nozaki, Bull. Chem. Soc. Jpn., 52, 1752 (1979).
24. a) J. A. Dale, D. L. Dull, and H. S. Mosher, J. Org. Chem., 34, 2543 (1969);
25. b) J. A. Dale and H. S. Mosher, J. Am. Chem. Soc., 95, 512 (1973).
26. M. Caron and K. B. Sharpless, J. Org. Chem., 50, 1557 (1985).
27. a) J.-L. Luche, J. Am. Chem. Soc., 100, 2226 (1978);
28. b) A. L. Gemal and J.-L. Luche, J. Am. Chem. Soc., 103, 5454 (1981).
29. a) T. Nakata, Y Tani, M. Hatozaki, and T. Oishi, Chem. Pharm. Bull., 32, 1411 (1984);
30. b) T. Oishi and T. Nakata, Acc. Chem. Res., 17, 338 (1984).
31. G. Stork and J. M. Poirier, J. Am. Chem. Soc., 105, 1073 (1983).
32. a) W. J. Scott and J. K. Stille, J. Am. Chem. Soc., 108, 3033 (1986);
33. b) W. J. Scott and J. E. McMurry, Acc. Chem. Res., 21, 47 (1988);
34. c) K. Ritter, Synthesis, 1993, 735.
35. For a review of cembranoids syntheses, see: M. A. Tius, Chem. Rev., 88, 719 (1988).
36. D. A. Evans, A. M. Ratz, B. E. Huff, and G. S. Sheppard, J. Am. Chem. Soc., 117, 3448 (1995).
37. B. D. Brandes and E. N. Jacobsen, J. Org. Chem., 59, 4378 (1994).
38. 2Mg complex has been used, as a catalyst, for polymerization of monomers. For example, see: C. W. Kamienski, N. C. Gastonia, and J. F. Eastham, U. S. Patent 3847883 (1974); Chem. Abstr., 82, 58590 (1975). The same complex has been used for metallation of substituted trifluoromethylbenzenes, see: G. Castaldi and G. Borsotti, European Patent 0491326A2; Chem. Abstr., 117, 150667 (1992).
39. 2Mg complex has been used, as a catalyst, for polymerization of monomers. For example, see: C. W. Kamienski, N. C. Gastonia, and J. F. Eastham, U. S. Patent 3847883 (1974); Chem. Abstr., 82, 58590 (1975). The same complex has been used for metallation of substituted trifluoromethylbenzenes, see: G. Castaldi and G. Borsotti, European Patent 0491326A2; Chem. Abstr., 117, 150667 (1992).
40. 2Mg complex has been used, as a catalyst, for polymerization of monomers. For example, see: C. W. Kamienski, N. C. Gastonia, and J. F. Eastham, U. S. Patent 3847883 (1974); Chem. Abstr., 82, 58590 (1975). The same complex has been used for metallation of substituted trifluoromethylbenzenes, see: G. Castaldi and G. Borsotti, European Patent 0491326A2; Chem. Abstr., 117, 150667 (1992).
41. 2Mg complex has been used, as a catalyst, for polymerization of monomers. For example, see: C. W. Kamienski, N. C. Gastonia, and J. F. Eastham, U. S. Patent 3847883 (1974); Chem. Abstr., 82, 58590 (1975). The same complex has been used for metallation of substituted trifluoromethylbenzenes, see: G. Castaldi and G. Borsotti, European Patent 0491326A2; Chem. Abstr., 117, 150667 (1992).