A short synthesis of polyhydroxylated piperidines by aldol reaction of chelated amino acid ester enolates

European Journal of Organic Chemistry

Volumn , Issue 9, 1998, Pages 1833-1840

  Kazmaier, Uli ^a   Grandel, Roland ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Aldol reactions; Amino acids; Chelated enolates; Glycosidase inhibitors; Piperidine alkaloids

Indexed keywords

EID: 0002056041     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199809)1998:9<1833::aid-ejoc1833>3.0.co;2-f     Document Type: Article

References (51)

1. M. L. Sinnott, Chem. Rev. 1990, 90, 1171-1202.
2. A. B. Hughes. A. J. Rudge, Nat. Prod. Rep. 1994, 11, 135-162.
3. [3a] D. D. Schmidt, W. Frommer, L. Müller, E. Truscheit, Naturwissenschaften 1979, 66, 584-585.
4. [3b] S. Murao, S. Miyata, Agric. Biol. Chem. 1980, 44, 219-221.
5. [4a] G. W. J. Fleet, N. G. Ramsden, D. R. Witty, Tetrahedron 1989, 45, 327-336.
6. [4b] E. W. Baxter, A. B. Reitz, J. Org. Chem. 1994, 59, 3175-3185.
7. [4c] K. H. Park, Y. J. Yoon, S. G. Lee, J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623.
8. [4d] N. Asano, H. Kizu, K. Oseki, E. Tomioka, K. Matsui, M. Okamoto. K. Baba, J. Med. Chem. 1995, 38, 2349-2356.
9. [4e] Y.-M. Xu, W.-S. Zhou, Tetrahedron Lett. 1996, 37, 1461-1462.
10. [4f] L. Poitout, Y. Le Merrer, J.-C. Depezay, Tetrahedron Lett. 1996, 37, 1609-1612.
11. L. E. Fellows, E. A. Bell, D. G. Lynn, F. J. Pilkicwicz, I. Miura, K. Nakanishi, J. Chem. Soc., Chem. Commun. 1979, 977-978.
12. [6a] U. Fuhrmann, E. Bause, G. Legler, H. Ploegh, Nature 1984, 307, 755-758.
13. [6b] A. D. Elbein, G. Legler, A. Tlusty, W. McDowell, R. Schwarz, Arch. Biochem. Biophvs. 1984, 235, 579-588.
14. S. V. Evans, L. E. Fellows, T. K. M. Shing, G. W. J. Fleet, Phytochemistry 1985, 24, 1953-1955.
15. [8a] R. C. Bernotas, B. Ganem, Tedrahedron Lett 1985, 26, 4981-4982.
16. [8b] B. P. Bashyal, H.-F. Chow, L. E. Fellows, G. W. J. Fleet, Tetrahedron 1987, 43, 415-422.
17. [8c] G. W. J. Fleet, L. E. Fellows, P. W. Smith, Tetrahedron 1987, 43, 979-790.
18. K. S. Manning, D. G. Lynn, J. Shabanowitz, L. E. Fellows, M. Singh, B. D. Shrire, J. Chem. Soc., Chem. Comm 1985, 127-129.
19. I. C. di Bello, P. Dorling, L. E. Fellow, B. Winchester, FEBS Lett. 1984, 176, 61.
20. [11a] S. Horii, H. Fukase, T. Matsuo, Y. Kameda; N. Asano, K. Matsui, J Med. Chem. 1986, 29, 1038-1046.
21. [11b] P. B. Anzeveno, L. J. Creemer, J. K. Daniel, C.-H. R. King, P. S. Liu, J. Org. Chem 1989, 54, 2539-2542.
22. [12a] M. J. Humphries, K. Matsumoto, S. L. White, K. Olden, Cancer Res. 1986, 46, 5215-5222.
23. [12b] J. W. Dennis, K. Koch, S. Yousefi, I. van der Elst, Cancer Res 1990, 50, 1867 1973.
24. [13a] F. M. Platt, G. R. Neises, R. A. Dwek, T. D. Butters J. Biol. Chem. 1994, 269, 8362-8365
25. [13b] T. M. Block, X. Lu, F. M. Platt, G. R. Foster, W. H. Gerlich, B. S. Blumberg, R. A. Dwek, Proc. Natl. Acad. Sci USA 1994, 91, 2235-2239.
26. [14a] T. Kajimoto, L. Chen, K. K.-C. Liu, C.-H. Wong, J. Am. Chem Soc. 1991, 113, 6678-6680.
27. [14b] R. H. Furneaux, P. C. Tyler, L. A. Whitehouse, Tetrahedron Lett. 1993, 34, 3609-3612.
28. [14c] L. Poitout, Y. Le Merrer, J.-C. Depezay, Tetrahedron Lett. 1994, 35, 3293-3296.
29. [14d] H.-J. Altenbach, K. Himmeldirk, Tetrahedron: Asymmetry 1995, 6, 1077-1080.
30. [14e] C. R. Johnson, A. Golebiowski, E. Schoffers, H. Sundram, M. P. Braun, Synleti 1995, 313-314.
31. [14f] A. I. Meyers, D. A. Price, C. J. Anders, Synlett 1997, 533-534.
32. [14g] F.-M. Kieß, P. Poggendorf, S. Picasso, V. Jäger, J. Chem. Soc., Chem. Commun. 1998, 119-120.
33. [15a] A. P. Nin, O. Varela, R. M. de Lederkremer, Tetrahedron 1993, 49, 9459-9464.
34. [15b] C. Herdeis, E. Heller, Tetrahedron: Asymmetry 1993, 4, 2085-2094.
35. R. Grandel, U. Kazmaier, Tetrahedron Lett. 1997, 38, 8009-8012.
36. R. Grandel, U. Kazmaier, F. Rominger, J. Org. Chem., in press.
37. U Kazmaier, Liebigs Ann. 1997, 285-295.
38. [19a] U. Kazmaier, R. Grandel, Synlett 1995, 945-946.
39. [19b] R Grandel, U. Kazmaier, B. Nuber, Liebigs Ann. 1996, 1143-1150.
40. R. Grandel, U. Kazmaier, Eur. J. Org. Chem 1998, 409-417.
41. S M. Weinreb, D. M. Demko, T. A. Lessen, Tetrahedron Lett. 1986, 27, 2099-2102.
42. [22a] M. Cherest, H. Felkin, N. Prudent, Tetrahedron Lett. 1968, 2199.
43. [22b] N. T. Anh, O. Eisenstein, Nouv J. Chim 1977, 1, 61
44. [22C] N. T. Anh, Top. Curr. Chem 1980, 88, 145.
45. L. M. Litvinenko, A. F. Popov, A. I. Bilobrova, M. K. Kudyrbaeva, J. Org. Chem. USSR 1979, 15, 467-471.
46. [24a] T. W. Bell, J. A. Ciaccio, J. Org. Chem. 1993, 55, 5153-5162.
47. [24b] J. A. Marshall, S. Beaudoin, J. Org. Chem. 1994, 59, 6614-6619.
48. [25a] O. Mitsunobu, Synthesis 1981, 1-28.
49. [25b] J. R. Henry, L. R. Marcin, M. C. McIntosh, P. M. Scola, G. D. Harris, S. M. Weinreb, Tetrahedron Lett. 1989, 30, 5709-5712.
50. Introduction of the THP protecting group results in the generation of a new stereogenic center (1:1) and therefore a second set of diastereomers (second set of signals in the NMR spectra). In the experimental section these diastereomers are reported as 4a, 4a′; 4b, 4b′ and so on. Because this chiral center has no influence on the stereochemical outcome of the reactions described, and because the protecting group is removed at the end of the synthesis, the THP protecting group is treated as an achiral protecting group in the context.
51. E. H. Gold, E. Babad, J. Org. Chem. 1972, 37, 2208-2210.