A Novel Short Convergent Entry into Himbacine Derivatives

Organic Letters

Volumn 4, Issue 9, 2002, Pages 1579-1582

  Van Cauwenberge, Gunther ^c   Gao, Ling Jie ^c   Van Haver, Dirk ^c   Milanesio, Marco ^b   Viterbo, Davide ^b   De Clercq, Pierre J ^a  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF EASTERN PIEDMONT   (Italy)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FURAN DERIVATIVE; HIMBACINE; MUSCARINIC RECEPTOR BLOCKING AGENT; NAPHTHALENE DERIVATIVE; PIPERIDINE DERIVATIVE;

ARTICLE; AUSTRALIA; CHEMICAL STRUCTURE; CHEMISTRY; MEDICINAL PLANT; PAPUA NEW GUINEA; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKALOIDS; AUSTRALIA; CRYSTALLOGRAPHY, X-RAY; FURANS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MUSCARINIC ANTAGONISTS; NAPHTHALENES; NEW GUINEA; PIPERIDINES; PLANTS, MEDICINAL; STEREOISOMERISM;

EID: 0037007744     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025801g     Document Type: Article

References (41)

1. (a) Brown, R. F. C.; Drummond, R.; Fogerty, A. C.; Hughes, G. K.; Pinhey, J. T.; Ritchie, E.; Taylor, W. C. Aust. J. Chem. 1956, 9, 283.
2. For a review, see: (b) Ritchie, E.; Taylor, W. C. The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, p 529.
3. For the total synthesis of himbacine, see: (a) Hart, D. J.; Wu, W.-L.; Kozikowski, A. P. J. Am. Chem. Soc. 1995, 117, 9369. Also see: Hart, D. J.; Li, J.; Wu, W. L.; Kozikowski, A. P. J. Org. Chem. 1997, 62, 5023.
4. For the total synthesis of himbacine, see: (a) Hart, D. J.; Wu, W.- L.; Kozikowski, A. P. J. Am. Chem. Soc. 1995, 117, 9369. Also see: Hart, D. J.; Li, J.; Wu, W. L.; Kozikowski, A. P. J. Org. Chem. 1997, 62, 5023.
5. (b) Chackalamannil, S.; Davies, R. J.; Asberom, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9812. Also see: Chackalamannil, S.; Davies, R. J.; Wang, Y.; Asberom, T.; Doller, D.; Wong, J.; Leone, D.; McPhail, A. T. J. Org. Chem. 1999, 64, 1932.
6. (b) Chackalamannil, S.; Davies, R. J.; Asberom, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9812. Also see: Chackalamannil, S.; Davies, R. J.; Wang, Y.; Asberom, T.; Doller, D.; Wong, J.; Leone, D.; McPhail, A. T. J. Org. Chem. 1999, 64, 1932.
7. (c) Takadoi, M.; Katoh, T.; Ishiwata, A. Terashima, S. Tetrahedron Lett. 1999, 40 3399.
8. (d) Hoffman, S.; Gao, L.-J.; Van Dingenen, H.; Hosten, N. G. C.; Van Haver, D.; De Clercq, P. J.; Milanesio, M.; Viterbo, D. Eur. J. Org. Chem. 2001, 2851.
9. For early studies directed toward the total synthesis of himbacine, see: (e) De Baecke, G.; De Clercq, P. J. Tetrahedron Lett. 1995, 36, 7515. Also see: Hofman, S.; De Baecke G.; Kenda, B.; De Clercq, P. J. Synthesis 1998, 479.
10. For early studies directed toward the total synthesis of himbacine, see: (e) De Baecke, G.; De Clercq, P. J. Tetrahedron Lett. 1995, 36, 7515. Also see: Hofman, S.; De Baecke G.; Kenda, B.; De Clercq, P. J. Synthesis 1998, 479.
11. (f) Baldwin, J. E.; Chesworth, R.; Parker, J. S.; Russell, T. Tetrahedron Lett. 1995, 36, 9551.
12. For a total synthesis of himandravine, see: Chackalamannil, S.; Davies, R.; McPhail, A. T. Org. Lett. 2001, 3, 1427.
13. (a) Darroch, S. A.; Taylor, W. C.; Choo, L. K.; Mitchelson, F. Eur. J. Pharmacol. 1990, 182, 131.
14. (b) Miller, J. H.; Aagaard, P. J.; Gibson, V. A.; McKinney, M. J. Pharmacol. Exp. Ther. 1992, 263, 663. For a classification of muscarine receptor subtypes, see: (c) Levey, A. I. Life Sci. 1993, 52, 441.
15. (b) Miller, J. H.; Aagaard, P. J.; Gibson, V. A.; McKinney, M. J. Pharmacol. Exp. Ther. 1992, 263, 663. For a classification of muscarine receptor subtypes, see: (c) Levey, A. I. Life Sci. 1993, 52, 441.
16. (a) Coyle, J. T.; Price, D. L.; DeLong, M. R. Science 1983, 219, 1184.
17. (b) Mash, D. C.; Flynn, D. D.; Potter, L. T. Science 1985, 228, 1115.
18. (a) Kozikowski, A. P.; Fauq, A. H.; Miller, J. H.; McKinney, M. Bioorg. Med. Chem. Lett. 1992, 2, 797.
19. (b) Malaska, M. J.; Fauq, A. H.; Kozikowski, A. P.; Aagard, P. J.; McKinney, M. Bioorg. Med. Chem. Lett. 1993, 3, 1247.
20. (c) Malaska, M. J.; Fauq, A. H.; Kozikowski, A. P.; Aagaard, P. J.; McKinney, M. Bioorg. Med. Chem. Lett. 1995, 5, 61.
21. (d) Doller, D.; Chackalamannil, S.; Czarnicki, M.; McQuade, R.; Ruperto, V. Bioorg. Med. Chem. Lett. 1999, 9, 901. Also see ref 4a.
22. For reviews on the IMDA reaction, see: (a) Fallis, A. G. Can. J. Chem. 1984, 62, 183.
23. (b) Ciganek, E. Org. React. 1984, 32, 1.
24. (c) Craig, D. Chem. Soc. Rev. 1987, 187.
25. (d) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 513.
26. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
27. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
28. 13C NMR, IR, and mass spectroscopic methods.
29. (a) Trost, B. M.; Mueller, T. J. J. J. Am. Chem. Soc. 1994, 116, 4985.
30. (b) Ku, Y.-Y.; Patel, R. R.; Elisseou, E. M; Sawick, D. Tetrahedron Lett. 1995, 36, 2733.
31. (c) Marshall, J. A.; Xie, S. J. Org. Chem. 1995, 60, 7230.
32. 4, LiCl, THF, 60°C, 79% yield), according to: Wulff, W. D.; Peterson, G. A.; Banta, W. E.; Chan, K. S.; Faron, K. L.; Gilbertson, S. R.; Kaesler, R. W.; Yang, D. C.; Murray, C. K. J. Org. Chem. 1986, 51, 277.
33. (a) Shen, W.; Wang, L. J. Org. Chem. 1999, 64, 8873.
34. See also: (b) Uenishi, J.; Matsui, K. Tetrahedron Lett. 2001, 42, 4353.
35. If is worth noting that it was possible to confirm the correct enantiomeric configuration by refinement of the absolute structure parameter, see: Flack, H. D. Acta Crystallogr. 1983, A39, 876. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-180241. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. [Fax: int.code +44 (1223) 336-033. E-mail: deposit@ ccdc.cam.ac.uk].
36. Calculated by the MM2* force field implementation of MacroModel, see: MacroModel-An Integrated Software System for Modeling Organic and Bioorganic Molecules using Molecular Mechanics. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
37. (a) He, J.-F.; Wu, Y.-L. Tetrahedron 1988, 44, 1933.
38. (b) White, J. D.; Demnitz, F. W. J.; Oda, H.; Hassler, C.; Snyder, J. P. Org. Lett. 2000, 2, 3313.
39. (c) Turner, C. I.; Williamson, R. M.; Paddon-Row: M. N.; Sherburn, M. S. J. Org. Chem. 2001, 66, 3963.
40. 2d according to (a) Capella, L.; Degl'Innocenti, A.; Mordini, A.; Reginato, G.; Ricci, A.; Seconi, G. Synthesis 1991, 1201.
41. (b) Heutringer, M. H.; Singer, R. D.; Oehlschlager, A. C. J. Am. Chem. Soc. 1990, 112, 9397.