Titanium-mediated cyclization of ω-vinyl imides in alkaloid synthesis: Isoretronecanol, trachelanthamidine, 5-epitashiromine, and tashiromine

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6771-6775

  Kim, Se Ho ^a   Kim, Seok In ^a   Lai, Sheng ^a   Cha, Jin Kun ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 EPITASHIROMINE; HELIOTRIDANE; INDOLIZIDINE ALKALOID; ISORETRONECANOL; METHYLINDOLIZIDINE; PSEUDOHELIOTRIDANE; PYRROLIZIDINE ALKALOID; TASHIROMINE; TRACHELANTHAMIDINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; HYDROGENATION; ISOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032886125     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9907383     Document Type: Article

References (42)

1. For pyrrolizidine alkaloids, see: (a) Numata, A.; Ibuka, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, 1987; Vol. 31, Chapter 6, p 193.
2. (b) Ikeda, M.; Sato, T.; Ishibashi, H. Heterocycles 1988, 27, 1465.
3. (c) Robins, D. J. Nat. Prod. Rep. 1989, 6, 221.
4. (d) Hudlicky, T.; Seoane, G.; Price, J. D.; Gadamasetti, K. G. Synlett 1990, 433.
5. (e) Dai, W.-M.; Nagao, Y.; Fujita, E. Heterocycles 1990, 30, 1231.
6. (f) Robins, D. J. Nat. Prod. Rep. 1993, 10, 487.
7. For indolizidine alkaloids, see: (a) Daly, J. W.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1986; Vol. 4.
8. (b) Rajeswari, S.; Chandrasekharan, S.; Govindachari, T. R. Heterocycles 1987, 25, 659.
9. (c) Takahata, H.; Momose, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, 1993; Vol. 44, Chapter 3, p 189.
10. (d) Michael, J. P. Nat. Prod. Rep. 1994, 11, 639.
11. For some representative examples of previous work, see: (a) Tufariello, J. J.; Lee, G. E. J. Am. Chem. Soc. 1980, 102, 373.
12. (b) Keck, G. E.; Nickell, D. G. J. Am. Chem. Soc. 1980, 102, 3632.
13. (c) Vedejs, E.; Martinez, G. R. J. Am. Chem. Soc. 1980, 102, 7993.
14. (d) Hart, D. J.; Tsai, Y.-M. J. Am. Chem. Soc. 1982, 104, 1430.
15. (e) Choi, J.-K.; Hart, D. J. Tetrahedron 1985, 41, 3959.
16. (f) Hiemstra, H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014.
17. (g) Hudlicky, T.; Frazier, J. O.; Seoane, G.; Tiedje, M.; Seoane, A.; Kwart, L. D.; Beal, C. J. Am. Chem. Soc. 1986, 108, 3755.
18. (h) Nagao, Y.; Dai, W.-M.; Ochiai, M.; Tsukagoshi, S.; Fujita, E. J. Am. Chem. Soc. 1988, 110, 289.
19. Keck, G. E.; Cressman, E. N. K.; Enholm, E. J. J. Org. Chem. 1989, 54, 4345.
20. (j) Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719 and references therein.
21. Lee, J.; Ha, J. D.; Cha, J. K. J. Am. Chem. Soc. 1997, 119, 8127.
22. (a) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244.
23. (b) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294.
24. (c) Kulinkovich, O. G.; Sorokin, V. L.; Kel'in, A. V. Zh. Org. Khim. 1993, 29, 66.
25. (a) For several imides, ether is the solvent of choice for the preparation of primary alcohols, whereas use of THF often results in varying amounts of the methyl compounds as byproducts: Sung, M. J.; Cha, J. K. Unpublished results.
26. (b) Kim, S.-H.; Cha, J. K. Unpublished results.
27. For a general review on reduction of enamines or enamides, see: Pitacco, G.; Valentin, E. In The Chemistry of Enamines; Rappoport, Z., Ed.; Wiley: New York, 1994; Chapter 17, p 923.
28. Cf. Secrist, J. A., III; Logue, M. W. J. Org. Chem. 1972, 37, 335.
29. For related hydrogenation of enamides or enamines, see: (a) Leonard, N. J.; Sato, T. J. Org. Chem. 1969, 34, 1066.
30. (b) Muchowski, J. M.; Nelson, P. H. Tetrahedron Lett. 1980, 21, 4585.
31. (c) Miyano, S.; Fujii, S.; Yamashita, O.; Toraishi, N.; Sumoto, K. J. Org. Chem. 1981, 46, 1737.
32. (a) The cis/trans nomenclature refers to the relative stereochemistry of the two methine hydrogens.
33. 3 reduction of iminium compounds, see: Ohnuma, T.; Tabe, M.; Shiiya, K.; Ban, Y. Tetrahedron Lett. 1983, 24, 4249.
34. For an elegant use of borane for blocking reactivity at the pyrrolizidine nitrogen, see: White, J. D.; Amedio, J. C., Jr.; Gut, S.; Ohira, S.; Jayasinghe, L. R. J. Org. Chem. 1992, 57, 2270.
35. The spectroscopic data of these target alkaloids 1-8 were found to be in excellent agreement with those reported in the literature: (a) Pandey, G.; Reddy, G. D.; Chakrabarti, D. J. Chem. Soc., Perkin Trans. 1 1996, 219 and Pandey, G.; Reddy, G. D. Tetrahedron Lett. 1992, 33, 6533.
36. The spectroscopic data of these target alkaloids 1-8 were found to be in excellent agreement with those reported in the literature: (a) Pandey, G.; Reddy, G. D.; Chakrabarti, D. J. Chem. Soc., Perkin Trans. 1 1996, 219 and Pandey, G.; Reddy, G. D. Tetrahedron Lett. 1992, 33, 6533.
37. (b) Knight, D. W.; Share, A. C.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1997, 2089. Hart, D. J.; Tsai, Y.-M. J. Am. Chem. Soc. 1984, 106, 8209. Mori, M.; Kanda, N.; Oda, I.; Ban, Y. Tetrahedron 1985, 41, 5465.
38. (b) Knight, D. W.; Share, A. C.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1997, 2089. Hart, D. J.; Tsai, Y.-M. J. Am. Chem. Soc. 1984, 106, 8209. Mori, M.; Kanda, N.; Oda, I.; Ban, Y. Tetrahedron 1985, 41, 5465.
39. (b) Knight, D. W.; Share, A. C.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1997, 2089. Hart, D. J.; Tsai, Y.-M. J. Am. Chem. Soc. 1984, 106, 8209. Mori, M.; Kanda, N.; Oda, I.; Ban, Y. Tetrahedron 1985, 41, 5465.
40. (c) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322.
41. (d) Pearson, W. H.; Walavalkar, R.; Schkeryantz, J. M.; Fang, W.-k.; Blickensdorf, J. D. J. Am. Chem. Soc. 1993, 115, 10183.
42. (e) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613.