Synthesis of (+)-casuarine

Journal of Organic Chemistry

Volumn 65, Issue 10, 2000, Pages 2875-2886

  Denmark, Scott E ^a   Hurd, Alexander R ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CASUARINE; GLYCOSIDASE INHIBITOR; PYRROLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ISOLATION PROCEDURE;

ALKALOIDS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; ENZYME INHIBITORS; GLYCOSIDE HYDROLASES; HYDROXYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PLANT EPIDERMIS; PYRROLES; PYRROLIZIDINE ALKALOIDS; STEREOISOMERISM;

EID: 0034685994     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991680v     Document Type: Article

References (60)

1. Nash, R. J.; Fellows, L. E.; Dring, J. V.; Fleet, G. W. J.; Derome, A. E.; Hamor, T. A.; Scofield, A. M.; Watkin, D. J. Tetrahedron Lett. 1988, 29, 2487.
2. Molyneux, R. J.; Benson, M.; Wong, R. Y.; Tropea, J. E.; Elbein, A. D. J. Nat. Prod. 1988, 51, 1198.
3. Nash, R. J.; Fellows, L. E.; Plant, A. C.; Fleet, G. W. J.; Derome, A. E.; Baird, P. D.; Hearty, M. P.; Scofield, A. M. Tetrahedron 1988, 44, 5959.
4. Nash, R. J.; Fellows, L. E.; Dring, J. V.; Fleet, G. W. J.; Girdhar, A.; Ramsden, N. G.; Peach, J. M.; Hegarty. M. P.; Scofield, A. M. Phytochemistry 1990, 29, 111.
5. Harris, C. M.; Harris, T. M.; Molyneux, R. J.; Tropea, J. E.; Elbein, A. D. Tetrahedron Lett. 1989, 30, 5685.
6. Nash, R. J.; Thomas, P. I.; Waigh, R. D.; Fleet, G. W. J.; Wormald, M. R.; Lilley, P. M de Q.; Watkin,. D. J. Tetrahedron Lett. 1994, 35, 7849.
7. Wormald, M. R.; Nash, R. J.; Watson, A. A.; Bhadoria, B. K.; Langford, R.; Sims, M.; Fleet, G. W. J. Carbohydr. Lett. 1996, 2, 169.
8. (a) Dennis, J. W. Cancer Res. 1986, 46, 5131.
9. (b) Humphries, K. J.; Matsumoto, K; White, S.; Olden, K. Cancer Res. 1986, 46, 5212.
10. (c) Ostrander, G. K.; Scribner, N. K.; Rohrschneider, L. R. Cancer Res. 1988, 48, 1091.
11. (a) Gruters, R. A.; Neefjes, J. J.; Termette, M.; de Goede, R. E. Y.; Tulp, A.; Huisman, H. G.; Miedema, F.; Ploegh, H. L. Nature 1987, 330, 74.
12. (b) Walker, B. D.; Kowalski, M.; Goh, W. C.; Kozarsky, K.; Krieger, M.; Rosen, C.; Rohrschneider, L.; Haseltine, W. A.; Sodroski, J. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 8210.
13. (c) Ratner, L. AIDS Res. Hum. Retroviruses 1992, 8, 165.
14. Glycosidase inhibition by polyhydroxylated alkaloids has been reviewed. Fellows, L. E.; Nash, R. J. Sci. Prog. (Oxford) 1990, 74, 245.
15. (a) Elbein, A. D.; Tropea, J. E.; Molyneux, R. J. US pat. Appl. US 289,907; Chem. Abstr. 1990, 713, 91444.
16. (b) Fellows, L. E.; Nash, R. J. PCT Int. Appl. WO 90, 12014; Chem. Abstr. 1991, 114, 143777.
17. Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Pan, Y. T.; Elbein, A. D.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 5869.
18. 1, was recently reported. Kato, A.; Adachi, I.; Miyauchi, M.; Ikeda, K.; Komae, T.; Kizu, H.; Kameda, Y.; Watson, A. A.; Nash, R. J.; Wormald, M. R.; Fleet, G. W. J.; Asano, N. Carbohydr. Res. 1999, 316, 95.
19. For previous natural product synthesis using tandem nitroalkene cycloadditions, see: (a) Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1994, 59, 5672. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Am. Chem. Soc. 1996, 118, 8266. (c) Denmark, S. E.; Thorarensen, A. J. Am. Chem. Soc. 1997, 119, 125. (d) Denmark, S. E.; Parker, D. L.; Dixon, J. A. J. Org. Chem. 1997, 62, 435. (e) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668. (f) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1997, 62, 1675. (g) Denmark, S. E.; Herbert, B. J. Am. Chem. Soc. 1998, 120, 7357. (h) Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046.
20. For previous natural product synthesis using tandem nitroalkene cycloadditions, see: (a) Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1994, 59, 5672. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Am. Chem. Soc. 1996, 118, 8266. (c) Denmark, S. E.; Thorarensen, A. J. Am. Chem. Soc. 1997, 119, 125. (d) Denmark, S. E.; Parker, D. L.; Dixon, J. A. J. Org. Chem. 1997, 62, 435. (e) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668. (f) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1997, 62, 1675. (g) Denmark, S. E.; Herbert, B. J. Am. Chem. Soc. 1998, 120, 7357. (h) Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046.
21. For previous natural product synthesis using tandem nitroalkene cycloadditions, see: (a) Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1994, 59, 5672. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Am. Chem. Soc. 1996, 118, 8266. (c) Denmark, S. E.; Thorarensen, A. J. Am. Chem. Soc. 1997, 119, 125. (d) Denmark, S. E.; Parker, D. L.; Dixon, J. A. J. Org. Chem. 1997, 62, 435. (e) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668. (f) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1997, 62, 1675. (g) Denmark, S. E.; Herbert, B. J. Am. Chem. Soc. 1998, 120, 7357. (h) Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046.
22. For previous natural product synthesis using tandem nitroalkene cycloadditions, see: (a) Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1994, 59, 5672. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Am. Chem. Soc. 1996, 118, 8266. (c) Denmark, S. E.; Thorarensen, A. J. Am. Chem. Soc. 1997, 119, 125. (d) Denmark, S. E.; Parker, D. L.; Dixon, J. A. J. Org. Chem. 1997, 62, 435. (e) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668. (f) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1997, 62, 1675. (g) Denmark, S. E.; Herbert, B. J. Am. Chem. Soc. 1998, 120, 7357. (h) Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046.
23. For previous natural product synthesis using tandem nitroalkene cycloadditions, see: (a) Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1994, 59, 5672. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Am. Chem. Soc. 1996, 118, 8266. (c) Denmark, S. E.; Thorarensen, A. J. Am. Chem. Soc. 1997, 119, 125. (d) Denmark, S. E.; Parker, D. L.; Dixon, J. A. J. Org. Chem. 1997, 62, 435. (e) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668. (f) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1997, 62, 1675. (g) Denmark, S. E.; Herbert, B. J. Am. Chem. Soc. 1998, 120, 7357. (h) Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046.
24. For previous natural product synthesis using tandem nitroalkene cycloadditions, see: (a) Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1994, 59, 5672. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Am. Chem. Soc. 1996, 118, 8266. (c) Denmark, S. E.; Thorarensen, A. J. Am. Chem. Soc. 1997, 119, 125. (d) Denmark, S. E.; Parker, D. L.; Dixon, J. A. J. Org. Chem. 1997, 62, 435. (e) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668. (f) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1997, 62, 1675. (g) Denmark, S. E.; Herbert, B. J. Am. Chem. Soc. 1998, 120, 7357. (h) Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046.
25. For previous natural product synthesis using tandem nitroalkene cycloadditions, see: (a) Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1994, 59, 5672. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Am. Chem. Soc. 1996, 118, 8266. (c) Denmark, S. E.; Thorarensen, A. J. Am. Chem. Soc. 1997, 119, 125. (d) Denmark, S. E.; Parker, D. L.; Dixon, J. A. J. Org. Chem. 1997, 62, 435. (e) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668. (f) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1997, 62, 1675. (g) Denmark, S. E.; Herbert, B. J. Am. Chem. Soc. 1998, 120, 7357. (h) Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046.
26. For previous natural product synthesis using tandem nitroalkene cycloadditions, see: (a) Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1994, 59, 5672. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Am. Chem. Soc. 1996, 118, 8266. (c) Denmark, S. E.; Thorarensen, A. J. Am. Chem. Soc. 1997, 119, 125. (d) Denmark, S. E.; Parker, D. L.; Dixon, J. A. J. Org. Chem. 1997, 62, 435. (e) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668. (f) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1997, 62, 1675. (g) Denmark, S. E.; Herbert, B. J. Am. Chem. Soc. 1998, 120, 7357. (h) Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046.
27. A preliminary report of this work has appeared: Denmark, S. E.; Hurd, A. R. Org. Lett. 1999, 1, 1311.
28. Denmark, S. E.; Schnute, M. E. J. Org. Chem. 1994, 59, 4576.
29. Denmark, S. E.; Seierstad, M.; Herbert B. J. Org. Chem. 1999, 64, 884.
30. (a) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694.
31. (b) Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C37.
32. (c) Fleming, L; Henning, R.; Flaut, H. J. Chem. Soc., Chem. Commun. 1984, 29.
33. (d) Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans, 1 1995, 317.
34. Denmark, S. E.; Herbert, B. J. Org. Chem. 2000, 65, 2887.
35. Denmark, S. E.; Hurd, A. R. J. Org. Chem. 1998, 63, 3045.
36. Schnute, M. E. Ph.D. Thesis, University of Illinois, Urbana, 1995.
37. Denmark, S. E.; Seierstad, M. J. Org. Chem. 1999, 64, 1610.
38. The combination of the vinyl silane (Z)-14 with the Lewis acid MAPh did produce a nitronate, but this decomposed before [3 + 2] cycloaddition with vinyl silane 10.
39. Limat, D.; Schlosser, M. Tetrahedron 1995, 51, 5799.
40. Diastereomeric ratio was determined by chiral stationary phase supercritical fluid chromatography (SFC).
41. (a) The synthesis of 23 is described in the Experimental Section using a chiral nonracemic dieneophile, but the X-ray crystal structure was obtained from diffraction of racemic material.
42. (b) The crystallographic coordinates of 23 have been deposited with the Cambridge Crystallographic Data Centre; deposition no. CCDC 136434.
43. (a) Peterson, D. J. J. Org. Chem. 1968, 33, 780.
44. (b) Ager, D. J. Synthesis 1984, 384.
45. (c) Ager, D. J. Org. React. 1990, 38, 1.
46. Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044.
47. Kolb, H. C.; Ley, S. V.; Slawin, A. M. Z.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1992, 2735.
48. Diastereomeric ratio was determined by NMR. The two major diastereomers are assumed to be facial diastereomers. It is uncertain whether the third diastereomer is an oxime geometric isomer or an acetal epimer.
49. (a) Denmark, S. E.; Moon, Y.-C.; Cramer, C. J.; Dappen, M. S.; Senanayake, C. B. W. Tetrahedron 1990, 46, 7373.
50. (b) Colvin, E. W.; Robertson, A. D.; Seebach, D.; Beck. A. K. J. Chem. Soc., Chem. Commun. 1981, 952.
51. Denmark, S. E.; Dixon, J. A. J. Org. Chem. 1998, 63, 6178.
52. Liu, J.; Niwayama, S.; You, Y.; Houk, K. N. J. Org. Chem. 1998, 63, 1064.
53. Dixon, J. A. Ph.D. Thesis, University of Illinois, Urbana, 1998.
54. Lewis, F. D.; Oxman, J. D.; Huffman, J. C. J. Am. Chem. Soc. 1984, 106, 466.
55. (a) Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1993, 115, 3133.
56. (b) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 256.
57. (c) Reetz, M. T. In Selectivities in Lewis Acid Promoted Reactions; Schiner, D.; Ed.; Kluwer: Dordrecht, 1989; pp 107-125.
58. Domingo, L. R.; Arnó, M.; Andrés, J. J. Org. Chem. 1999, 64, 5867.
59. Cornforth, J. W.; Cornforth, R. H.; Mathew, K. K. J. Chem. Soc. 1959, 112.
60. A5000 Raney Nickel was purchased from Activated Metals and Chemicals, Inc.