Total synthesis of ingenol

Journal of the American Chemical Society

Volumn 125, Issue 6, 2003, Pages 1498-1500

  Tanino, Keiji ^a   Onuki, Kei ^a   Asano, Kohei ^a   Miyashita, Masaaki ^a   Nakamura, Tsuyoshi ^b   Takahashi, Yoshinori ^b   Kuwajima, Isao ^c  

^a HOKKAIDO UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INGENOL;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

ALCOHOLS; DITERPENES; EPOXY COMPOUNDS; EUPHORBIA; STEREOISOMERISM;

EID: 0037433234     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029226n     Document Type: Article

References (31)

1. (a) Hecker, E. Cancer Res. 1968, 28, 2338.
2. (b) Zechmeister, K.; Brandl, F.; Hoffe, W.; Hecker, E.; Opferkuch, H. J.; Adolf, W. Tetrahedron Lett. 1970, 4075.
3. (c) Uemura, D.; Hirata, Y. Tetrahedron Lett. 1971, 3673.
4. For recent reviews on synthetic studies on ingenol, see: (a) Rigby, J. H. Stud. Nat. Prod. Chem. 1993, 12, 233. (b) Kim, S.; Winkler, J. D. Chem. Soc. Rev. 1997, 26, 387.
5. For recent reviews on synthetic studies on ingenol, see: (a) Rigby, J. H. Stud. Nat. Prod. Chem. 1993, 12, 233. (b) Kim, S.; Winkler, J. D. Chem. Soc. Rev. 1997, 26, 387.
6. (a) Kupchan, S. M.; Uchida, I.; Branfman, A. R.; Dailey, R. G.; Fei, B. Y. Science 1976, 191, 571.
7. (b) Hecker, E. Pure Appl. Chem. 1977, 49, 1423.
8. (c) Hasler, C. M.; Acs, G.; Blumberg, M. Cancer Res. 1992, 52, 202.
9. (d) Fujiwara, M.; Ijichi, K.; Tokuhisa, K.; Katsuura, K.; Shigeta, S.; Konno, K.; Wang, G.-Y.-S.; Uemura, D.; Yokota, T.; Baba, M. Antimicrob. Agents Chemother. 1996, 40, 271.
10. For recent reports that are not covered in ref 2, see: (a) Winkler, J. D.; Kim, S.; Harrison, S.; Lewin, N. E.; Blumberg, P. M. J. Am. Chem. Soc. 1999, 121, 296. (b) Kigoshi, H.; Suzuki, Y.; Aoki, K.; Uemura, D. Tetrahedron Lett. 2000, 41, 3927. (c) Tang, H.; Yusuff, N.; Wood, J. L. Org. Lett. 2001, 3, 1563. (d) Rigby, J. H.; Bazin, B.; Meyer, J. H.; Mohammadi, F. Org. Lett. 2002, 4, 799.
11. For recent reports that are not covered in ref 2, see: (a) Winkler, J. D.; Kim, S.; Harrison, S.; Lewin, N. E.; Blumberg, P. M. J. Am. Chem. Soc. 1999, 121, 296. (b) Kigoshi, H.; Suzuki, Y.; Aoki, K.; Uemura, D. Tetrahedron Lett. 2000, 41, 3927. (c) Tang, H.; Yusuff, N.; Wood, J. L. Org. Lett. 2001, 3, 1563. (d) Rigby, J. H.; Bazin, B.; Meyer, J. H.; Mohammadi, F. Org. Lett. 2002, 4, 799.
12. For recent reports that are not covered in ref 2, see: (a) Winkler, J. D.; Kim, S.; Harrison, S.; Lewin, N. E.; Blumberg, P. M. J. Am. Chem. Soc. 1999, 121, 296. (b) Kigoshi, H.; Suzuki, Y.; Aoki, K.; Uemura, D. Tetrahedron Lett. 2000, 41, 3927. (c) Tang, H.; Yusuff, N.; Wood, J. L. Org. Lett. 2001, 3, 1563. (d) Rigby, J. H.; Bazin, B.; Meyer, J. H.; Mohammadi, F. Org. Lett. 2002, 4, 799.
13. For recent reports that are not covered in ref 2, see: (a) Winkler, J. D.; Kim, S.; Harrison, S.; Lewin, N. E.; Blumberg, P. M. J. Am. Chem. Soc. 1999, 121, 296. (b) Kigoshi, H.; Suzuki, Y.; Aoki, K.; Uemura, D. Tetrahedron Lett. 2000, 41, 3927. (c) Tang, H.; Yusuff, N.; Wood, J. L. Org. Lett. 2001, 3, 1563. (d) Rigby, J. H.; Bazin, B.; Meyer, J. H.; Mohammadi, F. Org. Lett. 2002, 4, 799.
14. Winkler, J. D.; Rouse, M. B.; Greaney, M. F.; Harrison, S. J.; Jeon, Y. T. J. Am. Chem. Soc. 2002, 124, 9726.
15. Winkler, J. D.; Henegar, K. E. J. Am. Chem. Soc. 1987, 109, 2850.
16. Nakamura, T.; Matsui, T.; Tanino, K.; Kuwajima, I. J. Org. Chem. 1997, 62, 3032.
17. Tanino, K.; Nakamura, T.; Matsui, T.; Kuwajima, I. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1997, 39, 1.
18. Dalton, D. R.; Dutta, V. P.; Jones, D. C. J. Am. Chem. Soc. 1968, 90, 5498.
19. For examples of ring-enlargement reactions via rearrangement of an epoxy alcohol, see: (a) Maruoka, K.; Hasegawa, M.; Yamamoto, H.; Suzuki, K.; Shimazaki, M.; Tsuchihashi, G. J. Am. Chem. Soc. 1986, 108, 3827. (b) Tu, Y. Q.; Sun, L. D.; Wang, P. Z. J. Org. Chem. 1999, 64, 629.
20. For examples of ring-enlargement reactions via rearrangement of an epoxy alcohol, see: (a) Maruoka, K.; Hasegawa, M.; Yamamoto, H.; Suzuki, K.; Shimazaki, M.; Tsuchihashi, G. J. Am. Chem. Soc. 1986, 108, 3827. (b) Tu, Y. Q.; Sun, L. D.; Wang, P. Z. J. Org. Chem. 1999, 64, 629.
21. Bredereck, H.; Simchen, G.; Rebsdat, S.; Kantlehner, W.; Horn, P.; Wahl, R.; Hoffman, H.; Grieshaber, P. Ber. 1968, 101, 41. See also: Trast, B. M.; Preckel, M. J. Am. Chem. Soc. 1973, 95, 7862.
22. Bredereck, H.; Simchen, G.; Rebsdat, S.; Kantlehner, W.; Horn, P.; Wahl, R.; Hoffman, H.; Grieshaber, P. Ber. 1968, 101, 41. See also: Trast, B. M.; Preckel, M. J. Am. Chem. Soc. 1973, 95, 7862.
23. Murai, A.; Tanimoto, N.; Sakamoto, N.; Masamune, T. J. Am. Chem. Soc. 1988, 110, 1985.
24. Corey, E. J.; Kim, S. U. J. Am. Chem. Soc. 1972, 94, 7586.
25. (a) Tarhouni, R.; Kirschleger, B.; Rambaud, M.; Villieras, J. Tetrahedron Lett. 1984, 25, 835. (b) Sadhu, K. M.; Matteson, D. S. Tetrahedron Lett. 1986, 27, 795. Use of diiodomethane instead of dibromomethane or chloroiodomethane effected rapid formation of the epoxide at a low temperature.
26. (a) Tarhouni, R.; Kirschleger, B.; Rambaud, M.; Villieras, J. Tetrahedron Lett. 1984, 25, 835. (b) Sadhu, K. M.; Matteson, D. S. Tetrahedron Lett. 1986, 27, 795. Use of diiodomethane instead of dibromomethane or chloroiodomethane effected rapid formation of the epoxide at a low temperature.
27. Yasuda, A.; Tanaka, S.; Oshima, K.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1974, 96, 6513.
28. Eschinasi, E. H. J. Org. Chem. 1970, 35, 1598.
29. Murata, S.; Suzuki, M.; Noyori, R. J. Am. Chem. Soc. 1979, 101, 2738.
30. For a similar transformation, see: Concellón, J. M.; Llavona, L.; Bernad, P. L. Tetrahedron 1995, 51, 5573.
31. Reuss, R. H.; Hassner, A. J. Org. Chem. 1974, 39, 1785.