Studies Toward the Synthesis of Stemona Alkaloids; A Short Synthesis of the Tricydic Core of Tuberostemonines

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 739-742

  Goldstein, David M ^a   Wipf, Peter ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

STEMONA;

ALKALOID; INDOLE DERIVATIVE; STENINE; TUBEROSTEMONINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030050808     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02302-X     Document Type: Article

References (27)

1. Gotz, M.; Strunz, G.M. "Tuberostemonine and related compounds. Chemistry of the Stemona alkaloids." in Alkaloids (Wiesner, K., Ed.), MTP, International Review of Sciences, Organic Chemistry, Series one, Vol. 9, p. 143-160, Butterworths, London 1973.
2. (b) Lee, H.M.; Chen, K.K. J. Amer. Pharm. Assoc. 1940, 29, 391-94.
3. Wipf, P., Kim, Y. and Goldstein, D.M. J. Am. Chem. Soc. in press.
4. For previous synthetic studies on Stemona alkaloids see: (a) Haruna, M.; Kobayashi, T.; Ito, K Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1985, 27, 200. (b) Williams, D.R.; Brown, D.L.; Benbow, J.W. J. Am. Chem. Soc., 1989, 111, 1923-5. (c) Xiang, L.I.; Kozikowski, A.P. Synlett 1990, 279-81. (d) Chen, C.Y.; Hart, D.J. J. Org. Chem. 1990, 55, 6236-40. (e) Beddoes, R.L.; Davies, M.P.H.; Thomas, E.J. J. Chem. Soc., Chem. Commun. 1992, 538-540. (f) Martin, S.F.; Corbett, J.W. Synthesis 1992, 55-57. (g) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840-49. (h) Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773-76. (i) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417-20.
5. For previous synthetic studies on Stemona alkaloids see: (a) Haruna, M.; Kobayashi, T.; Ito, K Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1985, 27, 200. (b) Williams, D.R.; Brown, D.L.; Benbow, J.W. J. Am. Chem. Soc., 1989, 111, 1923-5. (c) Xiang, L.I.; Kozikowski, A.P. Synlett 1990, 279-81. (d) Chen, C.Y.; Hart, D.J. J. Org. Chem. 1990, 55, 6236-40. (e) Beddoes, R.L.; Davies, M.P.H.; Thomas, E.J. J. Chem. Soc., Chem. Commun. 1992, 538-540. (f) Martin, S.F.; Corbett, J.W. Synthesis 1992, 55-57. (g) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840-49. (h) Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773-76. (i) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417-20.
6. For previous synthetic studies on Stemona alkaloids see: (a) Haruna, M.; Kobayashi, T.; Ito, K Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1985, 27, 200. (b) Williams, D.R.; Brown, D.L.; Benbow, J.W. J. Am. Chem. Soc., 1989, 111, 1923-5. (c) Xiang, L.I.; Kozikowski, A.P. Synlett 1990, 279-81. (d) Chen, C.Y.; Hart, D.J. J. Org. Chem. 1990, 55, 6236-40. (e) Beddoes, R.L.; Davies, M.P.H.; Thomas, E.J. J. Chem. Soc., Chem. Commun. 1992, 538-540. (f) Martin, S.F.; Corbett, J.W. Synthesis 1992, 55-57. (g) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840-49. (h) Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773-76. (i) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417-20.
7. For previous synthetic studies on Stemona alkaloids see: (a) Haruna, M.; Kobayashi, T.; Ito, K Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1985, 27, 200. (b) Williams, D.R.; Brown, D.L.; Benbow, J.W. J. Am. Chem. Soc., 1989, 111, 1923-5. (c) Xiang, L.I.; Kozikowski, A.P. Synlett 1990, 279-81. (d) Chen, C.Y.; Hart, D.J. J. Org. Chem. 1990, 55, 6236-40. (e) Beddoes, R.L.; Davies, M.P.H.; Thomas, E.J. J. Chem. Soc., Chem. Commun. 1992, 538-540. (f) Martin, S.F.; Corbett, J.W. Synthesis 1992, 55-57. (g) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840-49. (h) Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773-76. (i) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417-20.
8. For previous synthetic studies on Stemona alkaloids see: (a) Haruna, M.; Kobayashi, T.; Ito, K Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1985, 27, 200. (b) Williams, D.R.; Brown, D.L.; Benbow, J.W. J. Am. Chem. Soc., 1989, 111, 1923-5. (c) Xiang, L.I.; Kozikowski, A.P. Synlett 1990, 279-81. (d) Chen, C.Y.; Hart, D.J. J. Org. Chem. 1990, 55, 6236-40. (e) Beddoes, R.L.; Davies, M.P.H.; Thomas, E.J. J. Chem. Soc., Chem. Commun. 1992, 538-540. (f) Martin, S.F.; Corbett, J.W. Synthesis 1992, 55-57. (g) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840-49. (h) Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773-76. (i) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417-20.
9. For previous synthetic studies on Stemona alkaloids see: (a) Haruna, M.; Kobayashi, T.; Ito, K Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1985, 27, 200. (b) Williams, D.R.; Brown, D.L.; Benbow, J.W. J. Am. Chem. Soc., 1989, 111, 1923-5. (c) Xiang, L.I.; Kozikowski, A.P. Synlett 1990, 279-81. (d) Chen, C.Y.; Hart, D.J. J. Org. Chem. 1990, 55, 6236-40. (e) Beddoes, R.L.; Davies, M.P.H.; Thomas, E.J. J. Chem. Soc., Chem. Commun. 1992, 538-540. (f) Martin, S.F.; Corbett, J.W. Synthesis 1992, 55-57. (g) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840-49. (h) Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773-76. (i) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417-20.
10. For previous synthetic studies on Stemona alkaloids see: (a) Haruna, M.; Kobayashi, T.; Ito, K Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1985, 27, 200. (b) Williams, D.R.; Brown, D.L.; Benbow, J.W. J. Am. Chem. Soc., 1989, 111, 1923-5. (c) Xiang, L.I.; Kozikowski, A.P. Synlett 1990, 279-81. (d) Chen, C.Y.; Hart, D.J. J. Org. Chem. 1990, 55, 6236-40. (e) Beddoes, R.L.; Davies, M.P.H.; Thomas, E.J. J. Chem. Soc., Chem. Commun. 1992, 538-540. (f) Martin, S.F.; Corbett, J.W. Synthesis 1992, 55-57. (g) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840-49. (h) Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773-76. (i) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417-20.
11. For previous synthetic studies on Stemona alkaloids see: (a) Haruna, M.; Kobayashi, T.; Ito, K Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1985, 27, 200. (b) Williams, D.R.; Brown, D.L.; Benbow, J.W. J. Am. Chem. Soc., 1989, 111, 1923-5. (c) Xiang, L.I.; Kozikowski, A.P. Synlett 1990, 279-81. (d) Chen, C.Y.; Hart, D.J. J. Org. Chem. 1990, 55, 6236-40. (e) Beddoes, R.L.; Davies, M.P.H.; Thomas, E.J. J. Chem. Soc., Chem. Commun. 1992, 538-540. (f) Martin, S.F.; Corbett, J.W. Synthesis 1992, 55-57. (g) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840-49. (h) Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773-76. (i) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417-20.
12. For previous synthetic studies on Stemona alkaloids see: (a) Haruna, M.; Kobayashi, T.; Ito, K Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1985, 27, 200. (b) Williams, D.R.; Brown, D.L.; Benbow, J.W. J. Am. Chem. Soc., 1989, 111, 1923-5. (c) Xiang, L.I.; Kozikowski, A.P. Synlett 1990, 279-81. (d) Chen, C.Y.; Hart, D.J. J. Org. Chem. 1990, 55, 6236-40. (e) Beddoes, R.L.; Davies, M.P.H.; Thomas, E.J. J. Chem. Soc., Chem. Commun. 1992, 538-540. (f) Martin, S.F.; Corbett, J.W. Synthesis 1992, 55-57. (g) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840-49. (h) Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773-76. (i) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417-20.
13. Wipf, P.; Kim, Y. Tetrahedron Lett. 1992, 33, 5477-80.
14. 3, 0°-22°C, in 90% yield.
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20. Prepared from commercially available cis-1,4-butenediol.
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25. equation presented
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27. 2N: 223.1572, found: 223.1570.