An approach to the narciclasine alkaloids via a quinone methide initiated cyclization reaction

Tetrahedron Letters

Volumn 38, Issue 46, 1997, Pages 7955-7958

  Angle, Steven R ^a   Wada, Tetsuo ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; NARCICLASINE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030828142     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10138-1     Document Type: Article

References (31)

1. On leave from Showa Denko K.K., Kanagawa, Japan.
2. For the isolation of narciclasine see: (a) Ceriotti, G. Nature 1967, 213, 595-596.
3. For the isolation of narciclasine see: (a) Ceriotti, G. Nature 1967, 213, 595-596. (b) Piozzi, F.; Fuganti, C.; Mondelli, R.; Ceriotti, G. Tetrahedron, 1968, 24, 1119-1131.
4. For the isolation of lycoricidine see: Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull. 1968, 16, 1860-1864.
5. For leading references to the isolation, characterization and biological activity of pancratistatin see: (a) Pettit, G.R.; Gaddamidi, V.; Herald, D.L.; Cragg, G.M.; Singh, S.B.; Schmidt, J.M.; Boettner, F.E.; Williams, M.; Sagawa, Y. J. Nat. Prod. 1986, 49, 995-1002.
6. (b) Pettit, G.R.; Gaddamidi, V.; Cragg, G.M.; Herald, D.L.; Sagawa, Y. J. Chem. Soc. Chem. Commun. 1984, 1693-1694.
7. (c) Pettit, G.R.; Gaddamidi, V.; Cragg, G.M. J. Nat. Prod. 1984, 47, 1018-1020.
8. (d) Torres-Labanderia, J.J.; Davignon, P.; Pitha, J. J. Pharm. Sci. 1990, 80, 384-385.
9. For the total synthesis of pancratistatin see: (a) Danishefsky, S.J.; Lee, J.Y. J. Am. Chem. Soc. 1989, 111, 4829-4837.
10. (b) Tian, X.R.; Hudlicky, T.; Konigsberger, K. J. Am. Chem. Soc. 1995, 117, 3643-3644.
11. (c) Trost, B.M.; Pulley, S.R. J. Am. Chem. Soc. 1995, 117, 10143-10144.
12. (d) Hudlicky, T.; Tian, X.R.; Konigsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752-10765.
13. For leading references to previous work on the synthesis of pancratistatin see: (a) Gauthier, D.R.; Bender, S.I. Tetrahedron Lett. 1996, 37, 13-16.
14. (b) Acena, J.L.; Arjona, O.; Iradier, F.; Plumet, J. Tetrahedron Lett. 1996, 37, 105-106.
15. (c) Doyle, T.J.; Vanderveer, D.; Haseltine, J. Tetrahedron Lett. 1995, 36, 6197-6200.
16. (d) Rigby, J.H.; Gupta, V. Synlett, 1995, 547-548.
17. (e) Park, T.K.; Danishefsky, S.J. Tetrahedron Lett. 1995, 36, 195-196.
18. (f) Angle, S.R.; Louie, M.S. Tetrahedron Lett. 1993, 34, 4751-4754.
19. For leading references to the synthesis of lycoricidine and narciclasine see: (a) lbn Ahmed, S.; Chretien, F.; Chapleur, Y.; Hajjaj, N. Heterocyclic Commun. 1997, 3, 135-138.
20. (b) Khaldi, M.; Chretien, F.; Chapleur, Y. Tetrahedron Lett. 1995, 36, 3003-3006.
21. (c) Keck, G.E.; Wager, T.T. J. Org. Chem. 1996, 61, 8366-8367.
22. (d) Banwell, M.G.; Cowden, C.J.; Gable, R.W. J. Chem. Soc. Perkin Trans. 1 1994, 3515-3518.
23. (e) For a nitro aldol based synthesis of lycoricidine see: Paulsen, H.; Stubbe, M. Tetrahedron Lett. 1982, 23, 3171-3174.
24. For a review on the synthesis of the narciclasine alkaloids see: Chapleur, Y.; Chrètien, F.; Khaldi, M. "Recent Developments in the Enantiospecific Synthesis of Amaryllidaceae Alkaloids" in Antibiotics and Antiviral Compounds: Chemical Synthesis and Modification, Krohn, K.; Kirst, H.A.; Maag, H. Eds.; VCH Publishers, New York; pp. 379-388.
25. 13C NMR, IR, MS, and HRMS.
26. (a) Park, J.H.; Kim, S. Chem. Lett. 1989, 629-632.
27. (b) Kim, S.; Kee, I.S.; Park, Y.H.; Park, J.H. Synlett 1991, 183-184.
28. McIntosh, M.C.; Weinreb, S.M. J. Org. Chem. 1993, 58, 4823-4832.
29. (a) Hanessian, S.; Kloss, J. Tetrahedron Lett. 1985, 26, 1261-1264.
30. (b) Eyer, M.; Seebach, D. J. Am. Chem. Soc. 1985, 107, 3601-3606.
31. Angle, S.R.; Arnaiz, D.O.; Boyce, J.P.; Frutos, R.P.; Louie, M.S.; Mattson-Arnaiz, H.L.; Rainier, J.D.; Turnbull, K.D.; Yang, W. J. Org. Chem. 1994, 59, 6322-6337.