Chiral synthesis of furanosesquiterpene, (+)-ipomeamarone

Heterocycles

Volumn 43, Issue 6, 1996, Pages 1287-1300

  Matsuo, Keizo ^a   Arase, Takahiko ^a   Ishida, Shigetoshi ^a   Sakaguchi, Yusuke ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011175540     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-96-7463     Document Type: Article

References (40)

1. H. Watanabe and H. Iwata, J. Agr. Chem. Soc. Jpn., 1952, 26, 180.
2. a) T. Kubota, H. Yamaguchi, K. Naya, and T. Matsuura, Nippon Kagaku Kaishi, 1952, 73, 897;
3. b) T. Kubota and T. Matsuura, ibid., 1953, 74, 248;
4. c) T. Kubota, T. Matsuura, and N. Ichikawa, ibid., 1954, 75, 447;
5. d) T. Kubota, T. Matsuura, and N. Ichikawa, J. Chem. Soc., 1958, 3667;
6. e) T. Kubota, Tetrahedron, 1958, 4, 68.
7. J. A. Schneider, K. Yoshihara, and K. Nakanishi, J. Chem. Soc., Chem. Commun., 1983, 352.
8. a) F. H. MacDowall, J. Chem. Soc., 1925, 127, 2200;
9. b) A. J. Birch, R. A. Massy-Westropp, S. E. Wright, T. Kubota, T. Matsuura, and M. D. Sutherland, Chem. Ind. , 1954, 902;
10. c) B. F. Hegarty, J. R. Kelly, R. J. Park, and M. D. Sutherland, Aust. J. Chem., 1970, 23, 107;
11. d) W. D. Hamilton, R. J. Park, G. J. Perry, and M. D. Sutherland, ibid., 1973, 26, 375.
12. a) K. Matsuo, Y. Hasuike, and H. Kado, Chem. Pharm. Bull., 1990, 38, 2847;
13. b) K. Matsuo and Y. Hasuike, Yakugaku Zasshi, 1990, 110, 555.
14. a) F. A. Denz and W. G. Hanger, J. Path. Bot., 1961, 81, 91;
15. b) L. T. Burka, L. Kuhnert, B. J. Wilson, and T. M. Harris, J. Am. Chem. Soc., 1977, 99, 2302;
16. c) K. Oba and I. Uritani, Plant Cell Physiol., 1979, 20, 819;
17. d) H. Inoue and I. Uritani, ibid., 1979, 20, 1307;
18. e) L. T. Burka, L. J. Felice, and S. W. Jackson, Phytochemistry, 1981, 20, 647.
19. a) T. Kubota and T. Matsuura, Chem. Ind., 1956, 521;
20. b) L. T. Burka, B. J. Wilson, and T. M. Haris, J. Org. Chem., 1974, 39, 2212;
21. c) K. Konko and M. Matsumoto, Tetrahedron Lett., 1976, 4363;
22. d) T. Hudlicky and T. C. Lovelace, Synth. Commun., 1990, 20, 1721.
23. a) T. Sugimura, K. Koguro, and A. Tai, Tetrahedron Lett., 1993, 34, 509;
24. b) H. Nemoto, T. Tanabe, M. Nagamochi, and K. Fukumoto, Heterocycles, 1993, 35, 707.
25. Parts of this work have been reported in a preliminary communification: K. Matsuo and T. Arase, Chem. Pharm. Bull., 1995, 43, 890.
26. D. Seebach, R. Naef, and G. Calderari, Tetrahedron, 1984, 40, 1313.
27. C. Huynh, F. Derguini-Boumechal, and G. Linstrumelle, Tetrahedron Lett., 1979, 1503.
28. S. Hanessian, A. Tehim, and P. Chen, J. Org. Chem., 1993, 58, 7768.
29. K. Krohn and I. Hamann, Liebigs Ann. Chem., 1988, 949.
30. J. M. Fortunate and B. Ganem, J. Org. Chem., 1976, 41, 2194.
31. Racemic lactone (15) is known; a) D. B. Collum, F. Mohamadi, and J. S. Hallock, J. Am. Chem. Soc., 1983, 105, 6882; b) C. Einhorn and J. L. Luche, J. Organomet. Chem., 1987, 322, 177; c) S. Baskaran, I. Islam, and S. Chandrasekaran, J. Org. Chem., 1990, 55, 891;
32. Racemic lactone (15) is known; a) D. B. Collum, F. Mohamadi, and J. S. Hallock, J. Am. Chem. Soc., 1983, 105, 6882; b) C. Einhorn and J. L. Luche, J. Organomet. Chem., 1987, 322, 177; c) S. Baskaran, I. Islam, and S. Chandrasekaran, J. Org. Chem., 1990, 55, 891;
33. Racemic lactone (15) is known; a) D. B. Collum, F. Mohamadi, and J. S. Hallock, J. Am. Chem. Soc., 1983, 105, 6882; b) C. Einhorn and J. L. Luche, J. Organomet. Chem., 1987, 322, 177; c) S. Baskaran, I. Islam, and S. Chandrasekaran, J. Org. Chem., 1990, 55, 891;
34. d) T. Shono, M. Ishifune, and S. Kashimura, Chem. Lett., 1990, 449.
35. Y. Fukuyama, Y. Kawashima, T. Miwa, and T. Tokoroyama, Synthesis, 1974, 443.
36. T. Tokoroyama, K. Matsuo, H. Kotsuki, and R. Kanazawa, Tetrahedron, 1980, 36, 3377.
37. R. A. Bell, M. B. Gravestock, and V. Y. Taguchi, Can. J. Chem., 1972, 50, 3749.
38. I. Ichimoto, K. Machiya, M. Kirihata, and H. Ueda, Agric. Biol. Chem., 1990, 54, 657.
39. L. Castellanos, J. Cleophax, C. Colas, S. D. Gero, J. Leboul, D. Mercier, A. Olesker, A. Rolland, B. Quiclet-Sire, and A. Sepulchre, Carbohydr. Res., 1980, 82, 283.
40. K. Mori, S. Sasaki, T. Tamada, T. Suguro, and S. Masuda, Tetrahedron, 1979, 35, 1601.