Synthetic Studies on Sesquiterpenoids from D-Glucose-Total Syntheses of (+)-Eremantholide A and (-)-Verrucarol-

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 56, Issue 12, 1998, Pages 1026-1035

  Takao, Ken Ichi ^a   Ishihara, Jun ^a,b   Tadano, Kin Ichi ^a  

^a KEIO UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

(+) eremantholide A; ( ) verrucarol; Consecutive quaternary carbon center; D glucose; Enantiopure building block; Enantiospecific total synthesis; Intramolecular Knoevenagel cyclization; Nine membered ring formation; Radical carbocyclization

Indexed keywords

EID: 0039906382     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.56.1026     Document Type: Article

References (43)

1. S. Hanessian, "Total Synthesis of Natural Products: The "Chiron" Approach", Pergamon Press, Oxford, 1983
2. K. Tadano, Y. Idogaki, H. Yamada, T. Suami, Chem. Lett., 1985, 1925; J. Org. Chem., 52, 1201 (1987)
3. K. Tadano, Y. Idogaki, H. Yamada, T. Suami, Chem. Lett., 1985, 1925; J. Org. Chem., 52, 1201 (1987)
4. K. Tadano, H. Yamada, Y. Idogaki, S. Ogawa, T. Suami, Tetrahedron, 46, 2353 (1990)
5. K. Tadano, S. Kanazawa, S. Ogawa, J. Org. Chem., 53, 3868 (1988)
6. K. Tadano, Y. Isshiki, M. Minami, S. Ogawa, J. Org. Chem., 58, 6266 (1993)
7. (b) K. Tadano, "Studies in Natural Products Chemistry", Vol. 10, ed. by Attaur-Rahman, Elsevier, Amsterdam, 1992, p. 405
8. (a) K. Takao, H. Ochiai, T. Hashizuka, H. Koshimura, K. Tadano, S. Ogawa, Tetrahedron Lett., 36, 1487 (1995);
9. (b) K. Takao, H. Ochiai, K. Yoshida, T. Hashizuka, H. Koshimura, K. Tadano, S. Ogawa, J. Org. Chem., 60, 8179 (1995)
10. (a) R.F. Raffauf, P.-K.C. Huang, P.W. Le Quesne, S.B. Levery, T.F. Brennan, J. Am. Chem. Soc., 97, 6884 (1975);
11. (b) P.W. Le Quesne, S.B. Levery, M.D. Menachery, T.F. Brennan, R.F. Raffauf, J. Chem. Soc., Perkin Trans. 1, 1978, 1572;
12. W. Herz, N. Kumar, W. Vichnewski, J.F. Blount, J. Org. Chem., 45, 2503 (1980)
13. (a) T.F. Tam, B. Fraser-Reid, J. Org. Chem., 45, 1344 (1980);
14. (b) P.G. McDougal, Y.-I. Oh, D. VanDerveer, ibid., 54, 91 (1989);
15. R.K. Boeckman, Jr., D.K. Heckendorn, R.L. Chinn, Tetrahedron Lett., 28, 3551 (1987);
16. D. Caine, M.E. Arant, ibid., 35, 6795 (1994)
17. R.K. Boeckman, Jr., S.K. Yoon, D.K. Heckendorn, J. Am. Chem. Soc., 113, 9682 (1991)
18. A.B. Smith, III, P.A. Levenberg, P.J. Jerris, R.M. Scarborough, Jr., P.M. Wovkulich, J. Am. Chem. Soc., 103, 1501 (1981)
19. S.H. Andersen, N.B. Das, R.D. Jorgensen, G. Kjeldsen, J.S. Knudsen, S.C. Sharma, K.B.G. Torssell, Acta Chem. Scand. B, 36, 1 (1982)
20. (a) J. Ishihara, R. Nonaka, Y. Terasawa, K. Tadano, S. Ogawa, Tetrahedron: Asymmetry, 5, 2217 (1994);
21. (b) J. Ishihara, R. Nonaka, Y. Terasawa, R. Shiraki, K. Yabu, H. Kataoka, Y. Ochiai, K. Tadano, Tetrahedron Lett., 38, 8311 (1997);
22. J. Ishihara, R. Nonaka, Y. Terasawa, R. Shiraki, K. Yabu, H. Kataoka, Y. Ochiai, K. Tadano, J. Org. Chem., 63, 2679 (1998)
23. T.W. Doyle, W.T. Bradner, "Anticancer Agents Based on Natural Products Models", eds. by J.M. Cassady, J.D. Douros, Academic, New York, 1980, p.43
24. (b) P.G. McDougal, N.R. Schmuff, "Progress in the Chemistry of Organic Natural Products", Vol. 47, eds. by W. Herz, H. Griesebach, G.W. Kirby, Ch. Tamm, Springer-Verlag, New York, 1985, p.153
25. (a) J. Gutzwiller, R. Mauli, H.P. Sigg, Ch. Tamm, Helv. Chim. Acta, 47, 2234 (1964);
26. (b) A.T. McPhail, G.A. Sim, Chem. Commun., 1965, 350; idem, J. Chem. Soc.
27. (b) A.T. McPhail, G.A. Sim, Chem. Commun., 1965, 350; idem, J. Chem. Soc.
28. (a) R.H. Schlessinger, R.A. Nugent, J. Am. Chem. Soc., 104, 1116 (1982);
29. (b) B.M. Trost, P.G. McDougal, ibid., 104, 6110 (1982); also B. M. Trost, P.G. McDougal, K.L. Haller, ibid., 106, 383 (1984);
30. (b) B.M. Trost, P.G. McDougal, ibid., 104, 6110 (1982); also B. M. Trost, P.G. McDougal, K.L. Haller, ibid., 106, 383 (1984);
31. W.R. Roush, T.E. D'Ambra, ibid., 105, 1058 (1983)
32. (a) T. Suami, K. Tadano, Y. Ueno, Y. Iimura, Chem. Lett., 1985, 37;
33. K. Tadano, H. Maeda, M. Hoshino, Y. Iimura, T. Suami, J. Org. Chem., 52, 1946 (1987);
34. K. Tadano, H. Kimura, S. Ogawa, Bull. Chem. Soc. Jpn., 62, 1355 (1989)
35. A.P. Krapcho, J.F. Weinmaster, J.M. Ellridge, E.G.E. Jahngen, Jr., A.J. Lovey, W.P. Stephens, J. Org. Chem., 43, 138 (1978)
36. D.H.R. Barton, S.W. McCombie, J. Chem. Soc., Perkin Trans. 1, 1975, 1574
37. A.P. Breen, J.A. Murphy, C.W. Patterson, N.F. Wooster, Tetrahedron, 49, 10643 (1993)
38. D.H.R. Barton, D. Crich, W.B. Motherwell, ibid., 41, 3901 (1985)
39. W. Breitenstein, Ch. Tamm, Helv. Chim. Acta, 60, 1522 (1977)