Reactions of aminopentadienal derivatives with 5,6-dihydropyridinium salts as an approach to manzamine alkaloids based upon biogenetic considerations

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7381-7387

  Jakubowicz, Karine ^a   Abdeljelil, Kamel Ben ^a   Herdemann, Matthias ^a   Martin, Marie Thérèse ^a   Gateau Olesker, Alice ^a   Al Mourabit, Ali ^a   Marazano, Christian ^a   Das, Bhupesh C ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; MANZAMINE A; PYRIDINIUM DERIVATIVE;

ARTICLE; BIOSYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS;

EID: 0033214301     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990604p     Document Type: Article

References (36)

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3. For a recent review on synthetic approaches to manzamines, see: Magnier, E.; Langlois, Y. Tetrahedron 1998, 54, 6201-6258. Total synthesis of manzamine A: (a) Winkler, J. D.; Axten, J. M. J. Am. Chem. Soc. 1998, 120, 6425-6426. (b) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866-867.
4. For a recent review on synthetic approaches to manzamines, see: Magnier, E.; Langlois, Y. Tetrahedron 1998, 54, 6201-6258. Total synthesis of manzamine A: (a) Winkler, J. D.; Axten, J. M. J. Am. Chem. Soc. 1998, 120, 6425-6426. (b) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866-867.
5. For comprehensive reviews, see: (a) Matzanke, N.; Gregg, R. J.; Weinreb, S. M. Org. Prep. Proc. Int. 1998, 30, 3-51. (b) Andersen, R. J.; Van Soest, R. W. M.; Kong, F. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon Press: Elsevier Science 1996; Vol. 10, pp 301-355. Tsuda, M.; Kobayashi, J. Heterocycles 1997, 46, 765-794. (d) Crews, P.; Cheng, X.-C.; Adamczeski, M.; Rodriguez, J.; Jaspar, M.; Schmitz, F. J.; Traeger, S. C.; Pordesimo, E. O. Tetrahedron 1994, 50, 13567-13574.
6. For comprehensive reviews, see: (a) Matzanke, N.; Gregg, R. J.; Weinreb, S. M. Org. Prep. Proc. Int. 1998, 30, 3-51. (b) Andersen, R. J.; Van Soest, R. W. M.; Kong, F. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon Press: Elsevier Science 1996; Vol. 10, pp 301-355. Tsuda, M.; Kobayashi, J. Heterocycles 1997, 46, 765-794. (d) Crews, P.; Cheng, X.-C.; Adamczeski, M.; Rodriguez, J.; Jaspar, M.; Schmitz, F. J.; Traeger, S. C.; Pordesimo, E. O. Tetrahedron 1994, 50, 13567-13574.
7. For comprehensive reviews, see: (a) Matzanke, N.; Gregg, R. J.; Weinreb, S. M. Org. Prep. Proc. Int. 1998, 30, 3-51. (b) Andersen, R. J.; Van Soest, R. W. M.; Kong, F. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon Press: Elsevier Science 1996; Vol. 10, pp 301-355. Tsuda, M.; Kobayashi, J. Heterocycles 1997, 46, 765-794. (d) Crews, P.; Cheng, X.-C.; Adamczeski, M.; Rodriguez, J.; Jaspar, M.; Schmitz, F. J.; Traeger, S. C.; Pordesimo, E. O. Tetrahedron 1994, 50, 13567-13574.
8. For comprehensive reviews, see: (a) Matzanke, N.; Gregg, R. J.; Weinreb, S. M. Org. Prep. Proc. Int. 1998, 30, 3-51. (b) Andersen, R. J.; Van Soest, R. W. M.; Kong, F. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon Press: Elsevier Science 1996; Vol. 10, pp 301-355. Tsuda, M.; Kobayashi, J. Heterocycles 1997, 46, 765-794. (d) Crews, P.; Cheng, X.-C.; Adamczeski, M.; Rodriguez, J.; Jaspar, M.; Schmitz, F. J.; Traeger, S. C.; Pordesimo, E. O. Tetrahedron 1994, 50, 13567-13574.
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10. For model reactions leading to keramaphidin B and halicyclamine A skeletons, see: (a) Baldwin, J. E.; Bischoff, L.; Claridge, T. D. W.; Heupel, F. A.; Spring, D. R.; Whitehead, R. Tetrahedron 1997, 53, 2271-2290 and references therein. (b) Gil, L.; Baucherel, X.; Martin, M.-T.; Marazano, C.; Das, B. C. Tetrahedron Lett. 1996, 36, 6231- 6234.
11. For model reactions leading to keramaphidin B and halicyclamine A skeletons, see: (a) Baldwin, J. E.; Bischoff, L.; Claridge, T. D. W.; Heupel, F. A.; Spring, D. R.; Whitehead, R. Tetrahedron 1997, 53, 2271-2290 and references therein. (b) Gil, L.; Baucherel, X.; Martin, M.-T.; Marazano, C.; Das, B. C. Tetrahedron Lett. 1996, 36, 6231-6234.
12. Kaiser, A.; Billot, X.; Gateau-Olesker, A.; Marazano, C.; Das, B. C. J. Am. Chem. Soc. 1998, 120, 0, 8026-8034.
13. Note that an aminopentadienal regioisomer of type 2 is required for construction of the manzamine A skeleton, while both isomers of type 2 and 3 can lead to the halicyclamine A skeleton (only the regioisomer of type 3 is shown in Scheme 2).
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17. 9
18. 9
19. Jakubowicz, K. Ph.D. Thesis in preparation.
20. Pure salts 1a,b were obtained from the corresponding methoxy adduct according to our reported procedure: Gil, L.; Gateau-Olesker, A.; Marazano, C.; Das, B. C. Tetrahedron Lett. 1995, 36, 707-710.
21. (a) All complex structures were resolved by intensive NMR spectroscopy studies including 1D and 2D NMR experiments (COSY 90, NOESY, HMQC, HMBC; see the Supporting Information). (b) Structure 17 was confirmed by an X-ray analysis that will be reported separately.
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27. Examples of push-pull dienes cycloadditions to classical dienophiles under high pressure: Branchadell, V.; Sodupe, M.; Ortuno, R. M.; Oliva, A.; Gomez-Pardo, D.; Guinguant, A.; d'Angelo, J. J. Org. Chem. 1991, 56, 4135-4141.
28. 4 in MeOH prior to acetylation gave the same results and is therefore unnecessary.
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30. Ben Abdeljelil, K. Ph.D. Thesis in preparation.
31. This model has recently received additional support by a short synthesis of keramaphidin B, albeit in low yield: Baldwin, J. E.; Claridge, T. D. W.; Culshaw, A. J.; Heupel, F. A.; Lee, V.; Spring, D. R.; Whitehead, R. C.; Boughtflower, R. J.; Mutton, I. M.; Upton, R. J. Angew. Chem., Int. Ed. 1998, 37, 2661-2663.
32. A pertinent definition has been formulated by C. H. Heathcock: "A particularly powerful strategy is "biomimetic synthesis", in which we try to guess how Nature might assemble a particular molecule and then try to mimic this hypothetical route in the laboratory".
33. For examples of particularly efficient biomimetic syntheses of natural alkaloids, see, inter alia: Robinson, R. J. Chem. Soc. 1917, 762. Heathcock, C. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 665- 681. François, D.; Lallemand, M.-C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Angew. Chem., Int. Ed. Engl. 1996, 37, 104-105. For a review with more examples, see: Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-312.
34. For examples of particularly efficient biomimetic syntheses of natural alkaloids, see, inter alia: Robinson, R. J. Chem. Soc. 1917, 762. Heathcock, C. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 665-681. François, D.; Lallemand, M.-C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Angew. Chem., Int. Ed. Engl. 1996, 37, 104-105. For a review with more examples, see: Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-312.
35. For examples of particularly efficient biomimetic syntheses of natural alkaloids, see, inter alia: Robinson, R. J. Chem. Soc. 1917, 762. Heathcock, C. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 665- 681. François, D.; Lallemand, M.-C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Angew. Chem., Int. Ed. Engl. 1996, 37, 104-105. For a review with more examples, see: Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-312.
36. For examples of particularly efficient biomimetic syntheses of natural alkaloids, see, inter alia: Robinson, R. J. Chem. Soc. 1917, 762. Heathcock, C. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 665- 681. François, D.; Lallemand, M.-C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Angew. Chem., Int. Ed. Engl. 1996, 37, 104-105. For a review with more examples, see: Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-312.