Studies relating to the structure of bruceoside C: Total synthesis of the alleged aglycon of bruceoside C

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5316-5325

  VanderRoest, James M ^a   Grieco, Paul A ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BRUCEOSIDE C; QUASSINOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 0029744579     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9605206     Document Type: Article

References (27)

1. Lee, K.-H.; Imakura, Y.; Huang, H.-C. J. Chem. Soc., Chem. Commun. 1977, 69. Lee, K.-H.; Imakura, Y.; Sumida, Y.; Wu, R. Y.; Hall, I. H.; Huang, H.-C. J. Org. Chem. 1979, 44, 2180. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Chem. Pharm. Bull. 1984, 32, 4702. Yoshimura, S.; Sakaki, T.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T. Bull. Chem. Soc. Jpn. 1985, 58, 2673. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1985, 58, 2680. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1986, 59, 3541. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Tetrahedron Lett. 1986, 27, 593. Yoshimura, S.; Ogawa, K.; Tsuyuki, T.; Takahashi, T.; Honda, T. Chem. Pharm. Bull. 1988, 36, 841.
2. Lee, K.-H.; Imakura, Y.; Huang, H.-C. J. Chem. Soc., Chem. Commun. 1977, 69. Lee, K.-H.; Imakura, Y.; Sumida, Y.; Wu, R. Y.; Hall, I. H.; Huang, H.-C. J. Org. Chem. 1979, 44, 2180. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Chem. Pharm. Bull. 1984, 32, 4702. Yoshimura, S.; Sakaki, T.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T. Bull. Chem. Soc. Jpn. 1985, 58, 2673. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1985, 58, 2680. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1986, 59, 3541. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Tetrahedron Lett. 1986, 27, 593. Yoshimura, S.; Ogawa, K.; Tsuyuki, T.; Takahashi, T.; Honda, T. Chem. Pharm. Bull. 1988, 36, 841.
3. Lee, K.-H.; Imakura, Y.; Huang, H.-C. J. Chem. Soc., Chem. Commun. 1977, 69. Lee, K.-H.; Imakura, Y.; Sumida, Y.; Wu, R. Y.; Hall, I. H.; Huang, H.-C. J. Org. Chem. 1979, 44, 2180. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Chem. Pharm. Bull. 1984, 32, 4702. Yoshimura, S.; Sakaki, T.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T. Bull. Chem. Soc. Jpn. 1985, 58, 2673. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1985, 58, 2680. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1986, 59, 3541. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Tetrahedron Lett. 1986, 27, 593. Yoshimura, S.; Ogawa, K.; Tsuyuki, T.; Takahashi, T.; Honda, T. Chem. Pharm. Bull. 1988, 36, 841.
4. Lee, K.-H.; Imakura, Y.; Huang, H.-C. J. Chem. Soc., Chem. Commun. 1977, 69. Lee, K.-H.; Imakura, Y.; Sumida, Y.; Wu, R. Y.; Hall, I. H.; Huang, H.-C. J. Org. Chem. 1979, 44, 2180. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Chem. Pharm. Bull. 1984, 32, 4702. Yoshimura, S.; Sakaki, T.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T. Bull. Chem. Soc. Jpn. 1985, 58, 2673. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1985, 58, 2680. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1986, 59, 3541. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Tetrahedron Lett. 1986, 27, 593. Yoshimura, S.; Ogawa, K.; Tsuyuki, T.; Takahashi, T.; Honda, T. Chem. Pharm. Bull. 1988, 36, 841.
5. Lee, K.-H.; Imakura, Y.; Huang, H.-C. J. Chem. Soc., Chem. Commun. 1977, 69. Lee, K.-H.; Imakura, Y.; Sumida, Y.; Wu, R. Y.; Hall, I. H.; Huang, H.-C. J. Org. Chem. 1979, 44, 2180. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Chem. Pharm. Bull. 1984, 32, 4702. Yoshimura, S.; Sakaki, T.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T. Bull. Chem. Soc. Jpn. 1985, 58, 2673. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1985, 58, 2680. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1986, 59, 3541. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Tetrahedron Lett. 1986, 27, 593. Yoshimura, S.; Ogawa, K.; Tsuyuki, T.; Takahashi, T.; Honda, T. Chem. Pharm. Bull. 1988, 36, 841.
6. Lee, K.-H.; Imakura, Y.; Huang, H.-C. J. Chem. Soc., Chem. Commun. 1977, 69. Lee, K.-H.; Imakura, Y.; Sumida, Y.; Wu, R. Y.; Hall, I. H.; Huang, H.-C. J. Org. Chem. 1979, 44, 2180. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Chem. Pharm. Bull. 1984, 32, 4702. Yoshimura, S.; Sakaki, T.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T. Bull. Chem. Soc. Jpn. 1985, 58, 2673. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1985, 58, 2680. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1986, 59, 3541. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Tetrahedron Lett. 1986, 27, 593. Yoshimura, S.; Ogawa, K.; Tsuyuki, T.; Takahashi, T.; Honda, T. Chem. Pharm. Bull. 1988, 36, 841.
7. Lee, K.-H.; Imakura, Y.; Huang, H.-C. J. Chem. Soc., Chem. Commun. 1977, 69. Lee, K.-H.; Imakura, Y.; Sumida, Y.; Wu, R. Y.; Hall, I. H.; Huang, H.-C. J. Org. Chem. 1979, 44, 2180. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Chem. Pharm. Bull. 1984, 32, 4702. Yoshimura, S.; Sakaki, T.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T. Bull. Chem. Soc. Jpn. 1985, 58, 2673. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1985, 58, 2680. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1986, 59, 3541. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Tetrahedron Lett. 1986, 27, 593. Yoshimura, S.; Ogawa, K.; Tsuyuki, T.; Takahashi, T.; Honda, T. Chem. Pharm. Bull. 1988, 36, 841.
8. Lee, K.-H.; Imakura, Y.; Huang, H.-C. J. Chem. Soc., Chem. Commun. 1977, 69. Lee, K.-H.; Imakura, Y.; Sumida, Y.; Wu, R. Y.; Hall, I. H.; Huang, H.-C. J. Org. Chem. 1979, 44, 2180. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Chem. Pharm. Bull. 1984, 32, 4702. Yoshimura, S.; Sakaki, T.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T. Bull. Chem. Soc. Jpn. 1985, 58, 2673. Sakaki, T.; Yoshimura, S.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1985, 58, 2680. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Bull. Chem. Soc. Jpn. 1986, 59, 3541. Sakaki, T.; Yoshimura, S.; Tsuyuki, T.; Takahashi, T.; Honda, T.; Nakanishi, T. Tetrahedron Lett. 1986, 27, 593. Yoshimura, S.; Ogawa, K.; Tsuyuki, T.; Takahashi, T.; Honda, T. Chem. Pharm. Bull. 1988, 36, 841.
9. Fukamiya, N.; Okano, M.; Miyamoto, M.; Tagahara, K.; Lee, K.-H. J. Nat. Prod. 1992, 55, 468.
10. Polonsky, J. Fortschr. Naturst. 1973, 30, 101. Yoshimura, S.; Sakaki, T.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T. Bull. Chem. Soc. Jpn. 1985, 58, 2573. Wani, M. C.; Taylor, H. T.; Thompson, J. B.; Wall, M. W. Lloydia 1978, 40, 578.
11. Polonsky, J. Fortschr. Naturst. 1973, 30, 101. Yoshimura, S.; Sakaki, T.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T. Bull. Chem. Soc. Jpn. 1985, 58, 2573. Wani, M. C.; Taylor, H. T.; Thompson, J. B.; Wall, M. W. Lloydia 1978, 40, 578.
12. Polonsky, J. Fortschr. Naturst. 1973, 30, 101. Yoshimura, S.; Sakaki, T.; Ishibashi, M.; Tsuyuki, T.; Takahashi, T.; Honda, T. Bull. Chem. Soc. Jpn. 1985, 58, 2573. Wani, M. C.; Taylor, H. T.; Thompson, J. B.; Wall, M. W. Lloydia 1978, 40, 578.
13. VanderRoest, J. M.; Grieco, P. A. J. Am. Chem. Soc. 1993, 115, 5841.
14. Unpublished results of J. M. VanderRoest, Indiana University.
15. Freeman, D.; Acher, A.; Mazur, Y. Tetrahedron Lett. 1975, 261. Also see. Grieco, P. A.; Inanaga, J.; Sham, H. L.; Sasaki, S.; Kim, H. J. Chem. Soc., Chem. Commun. 1987, 1044. Barton, D. H. R.; Hesse, R. H.; Pecht, M. M.; Rizzardo, E. J. Am. Chem. Soc. 1973, 95, 2748.
16. Freeman, D.; Acher, A.; Mazur, Y. Tetrahedron Lett. 1975, 261. Also see. Grieco, P. A.; Inanaga, J.; Sham, H. L.; Sasaki, S.; Kim, H. J. Chem. Soc., Chem. Commun. 1987, 1044. Barton, D. H. R.; Hesse, R. H.; Pecht, M. M.; Rizzardo, E. J. Am. Chem. Soc. 1973, 95, 2748.
17. Freeman, D.; Acher, A.; Mazur, Y. Tetrahedron Lett. 1975, 261. Also see. Grieco, P. A.; Inanaga, J.; Sham, H. L.; Sasaki, S.; Kim, H. J. Chem. Soc., Chem. Commun. 1987, 1044. Barton, D. H. R.; Hesse, R. H.; Pecht, M. M.; Rizzardo, E. J. Am. Chem. Soc. 1973, 95, 2748.
18. Calculations were carried out on a Silicon Graphics workstation using the MMX version of Allinger's MM2 program (Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127). Gajewski, J. J.; Gilbert, K. E.; McKelvey, J. Advances in Molecular Modelling; JAI Press: New York, 1990; pp 65-92.
19. Calculations were carried out on a Silicon Graphics workstation using the MMX version of Allinger's MM2 program (Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127). Gajewski, J. J.; Gilbert, K. E.; McKelvey, J. Advances in Molecular Modelling; JAI Press: New York, 1990; pp 65-92.
20. Node, M.; Ohta, K.; Kajimoto, T.; Nishide, K.; Fujita, E.; Fuji, K. Chem. Pharm. Bull. 1983, 31, 4178.
21. Miyashita, M.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772.
22. Swern, D.; Mancuso, A. J.; Huang, S.-L. J. Org. Chem. 1978, 43, 2480.
23. -3 (for Z = 2). Data were collected using a standard moving crystal, moving detector technique with fixed background counts at each extreme of the scan. Data were corrected for Lorentz and polarization terms and equivalent data averaged. The structure was solved by direct methods (MULTAN78) and Fourier techniques. For more information contact Dr. John C. Huffman, Indiana University Department of Chemistry, Molecular Structure Center, Bloomington, IN, 47405, Report Number 94033. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
24. Rubottom, G. M.; Graber, J. M. J. Org. Chem. 1978, 43, 1599.
25. For the synthesis of 26 see: Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
26. For the use of 26 as an oxidizing agent in organic chemistry see: Grieco, P. A.; Collins, J. L.; Moher, E. D.; Fleck, T. J.; Gross, R. S. J. Am. Chem. Soc. 1993, 115, 6078. Grieco, P. A.; Piñeiro-Nuñez, M. M. J. Am. Chem. Soc. 1994, 116, 7606. Also see reference 4.
27. For the use of 26 as an oxidizing agent in organic chemistry see: Grieco, P. A.; Collins, J. L.; Moher, E. D.; Fleck, T. J.; Gross, R. S. J. Am. Chem. Soc. 1993, 115, 6078. Grieco, P. A.; Piñeiro-Nuñez, M. M. J. Am. Chem. Soc. 1994, 116, 7606. Also see reference 4.