A novel sequential aminodiene Diels-Alder strategy for the rapid construction of substituted analogues of Kornfeld's Ketone

Organic Letters

Volumn 4, Issue 23, 2002, Pages 4135-4137

  Bur, Scott K ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; KETONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; KINETICS; SYNTHESIS;

INDICATORS AND REAGENTS; KETONES; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 0037078841     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0268992     Document Type: Article

References (34)

1. Saxton, J. E. Nat. Prod. Rep. 1993, 10, 349-395.
2. Ninomiya, I.; Kigichi, T. In The Alkaoids; Brossi, A., Ed.; Academic Press: San Diego, CA, 1990; Vol. 38, pp 1-156.
3. Somei, M.; Yokoyama, Y.; Murakami, Y. In The Alkaloids; Academic Press: San Diego, CA, 2000; Vol. 54, pp 191-257.
4. Jones, J. H. U.S. 4238486, 1980.
5. Yamamoto, I.; Itoh, M.; Shimojo, M.; Yumiya, Y.; Mukaihira, T.; Akada, Y. WO 9745410, 1997.
6. Mantegani, S.; Brambilla, E.; Enzo, C.; Damiani, G.; Fomaretto, M. G.; McArthur, R. A.; Varisi, M. Bioorg. Med. Chem. Lett. 1998, 8, 1117-1122.
7. Uhle, F. C. J. Am. Chem. Soc. 1949, 71, 761-766.
8. Teranishi, K.; Hayashi, S.; Natkatsuka, S.-i.; Goto, T. Synthesis 1995, 506-508.
9. (a) Kornfeld, E. C.; Fornefeld, E. J.; Kline, G. B.; Mann, M. J.; Jones, R. G.; Woodward, R. B. J. Am. Chem. Soc. 1954, 76, 5256-5257.
10. (b) Kornfeld, E. C.; Fornefeld, E. J.; Kline, G. B.; Mann, M. J.; Morrison, D. E.; Jones, R. G.; Woodward, R. B. J. Am. Chem. Soc. 1956, 78, 3087.
11. (a) Armstrong, V. W.; Coulton, S.; Ramage, R. Tetrahedron Lett. 1976, 4311-4314.
12. (b) Kurihara, T.; Terada, T.; Yoneda, R. Chem. Pharm. Bull. 1986, 34, 442-443.
13. (c) Kurihara, T.; Terada, T.; Harusawa, S.; Yoneda, R. Chem. Pharm. Bull. 1987, 35, 4793-4802.
14. (d) Matsubara, Y.; Yoneda, R.; Harusawa, S.; Kurihara, T. Chem. Pharm. Bull. 1988, 36, 1597-1600.
15. (e) Cacchi, S.; Ciattini, G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1988, 29, 3117-3120.
16. (f) Okide, G. B. Tetrahedron 1993, 49, 9517-9524.
17. (g) Carr, M. A.; Creviston, P. E.; Hutchison, D. R.; Kennedy, J. H.; Khau, V. V.; Kress, T. J.; Leanna, M. R.; Marshall, J. D.; Martinelli, M. J.; Peterson, B. C.; Varie, D. L.; Wepsiec, J. P. J. Org. Chem. 1997, 62, 8640-8653.
18. For an interesting derivative of 7 see: Waldvogel, E.; Engeli, P.; Kusters, E. Helv. Chim. Acta 1997, 80, 2084-2099.
19. Gribble, G. W. J. Chem. Soc., Perkin. Trans. 1 2000, 1045-1075.
20. (a) Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T. J. Org. Chem. 1997, 62, 4088-4096.
21. (b) Padwa, A.; Brodney, M. A.; Dimitroff, M. J. Org. Chem. 1998, 63, 5304-5305.
22. (c) Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T. J. Org. Chem. 1998, 63, 3986-3997.
23. (d) Padwa, A.; Brodney, M. A.; Satake, K.; Straub, C. S. J. Org. Chem. 1999, 64, 4617-4626.
24. Padwa, A.; Brodney, M. A.; Dimitroff, M. J. Org. Chem. 1998, 63, 3986-3937.
25. (a) Janey, J. M.; Iwama, T.; Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 2000, 65, 9059-9068.
26. (b) Kozmin, S. A.; Janey, J. M.; Rawal, V. H. J. Org. Chem. 1999, 64, 3039-3052.
27. Kozmin, S. A.; He, S.; Rawal, V. H. Org. Synth. 2001, 78, 152-159. This reagent has recently become commercially available.
28. Padwa, A.; Brodney, M. A.; Lynch, S. M. Org. Synth. 2000, 78, 202-211.
29. Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595-3607.
30. Yakushijin, K.; Suzuki, R.; Hattori, R.; Furukawa, H. Heterocycles 1981, 16, 1157-1160.
31. Laganis, E. D.; Chenard, B. L. Tetrahedron Lett. 1984, 25, 5831.
32. Kochi, J. K. Org. React. 1972, 19, 279-421.
33. Stereochemical assignments are based upon coupling constants for the C(4) proton in each diastereomer.
34. Hay, L. A.; Koenig, T. M.; Ginah, F. O.; Copp, J. D.; Mitchell, D. J. Org. Chem. 1998, 63, 5050-5058.