Transformation of D-glucal to (2S)-hydroxymethyl-dihydropyridones as intermediates to piperidine alkaloids

Synthesis

Volumn , Issue 11, 1999, Pages 1889-1892

  Koulocheri, Sofia D ^a   Haroutounian, Serkos A ^a  

^a AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

Asymmetric synthesis; D glucal; Dihydropyridone; Piperidine alkaloids

Indexed keywords

GLUCONATE CALCIUM; PIPERIDINE DERIVATIVE; PYRIDONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; REACTION ANALYSIS; SYNTHESIS;

EID: 0032746859     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3604     Document Type: Article

References (34)

1. de Raadt, A.; Ekhart, C. W.; Ebner, M.; Stütz, A. E. In Topics in Current Chemistry; Vol. 187; Driguez, H.; Thieme, J., Eds.; Springer Verlag: Berlin Heidelberg; 1997, p 158.
2. (a) Bernacki, R. J.; Korytnyk, W. Cancer Metastasis Rev. 1985, 4, 81.
3. (b) Tsukamoto, K.; Uno, A.; Shimada, S.; Imokaw, G. Clin. Res. 1989, 37A, 722.
4. (a) Fleet, G. W. J. FEBS Lett. 1988, 237.
5. (b) Gruters, R. A.; Neefjes, J. J.; Tersmette, M.; de Goede, R. E. Y.; Tulp, A.; Huisman, H. G.; Miedema, F.; Ploegh, H. L. Nature 1987, 330, 74.
6. For recent reviews see: (a) Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 633.
7. (b) Nadin, A. Contemp. Org. Synth. 1997, 4, 387.
8. (c) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825.
9. For selective recent reports see: (a) Herdeis, C.; Schiffer, T. Tetrahedron 1999, 55, 1043,
10. (b) Ichikawa, Y.; Igarashi, Y.; Ichikawa M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007.
11. (c) Wrodnigg, T, M.; Stütz, A. E.; Withers, S. G. Tetrahedron Lett. 1997, 38, 5463.
12. (d) Wong, C.-H.; Provencher, L.; Porco, J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492.
13. (e) Ryu, Y.; Kim, G. J. Org. Chem. 1995, 60, 103.
14. For selective recent reports see: (a) Kirhara, M.; Nishio, T.; Yokohama, S.; Kakuda, H.; Momose, T. Tetrahedron 1999, 55, 2911.
15. (b) Schürer, S. C.; Blechert, S. Tetrahedron Lett. 1999, 40, 1877.
16. (c) Ruiz, M.; Ruanova, T. M.; Ojea, V.; Quintela, J. M. Tetrahedron Lett. 1999, 40, 2021.
17. (d) Takahata, H.; Yotsui, Y.; Momose, T. Tetrahedron 1998, 54, 13505.
18. (e) Calvez, O.; Chiarioni, A.; Langlois, N. Tetrahedron Lett. 1998, 39, 9447.
19. (f) Cossy, J.; Dumas, C.; Pardo, D. G. Synlett 1997, 905.
20. (g) Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586.
21. Altenbach, H-J.; Wischnat, R. Tetrahedron Lett. 1995, 36, 4983.
22. (a) Zhou, W. S.; Lu, Z. H.; Wang, Z. M. Tetrahedron 1993, 49, 2641.
23. (b) Hopman, J. C. P.; Van den Berg, E.; Ollero Ollero, L.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1995, 36, 4315.
24. Ciufolini, M. A.; Wood, C. Y. Tetrahedron Lett. 1986, 27, 5085.
25. (a) Achmatowicz, O.; Bukowsky, P.; Szechner, B.; Zwierchowska, Z.; Zamojski, A. Tetrahedron 1971, 27, 1973.
26. (b) Levebvre, Y. Tetrahedron Lett. 1972, 133.
27. (c) Martin, S. F.; Guinn, D. E. J. Org. Chem. 1987, 52, 5588.
28. (d) Georgiadis, M. P.; Couladouros, E. A. J. Org. Chem. 1986, 57, 2725.
29. (a) Yang, C.-F.; Xu, Y.-M.; Lao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227.
30. (b) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659.
31. Hauser, F. M.; Ellenberger, S. R.; Ellenberger, W. P. Tetrahedron Lett. 1988, 29, 4939.
32. (a) Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592.
33. (b) Ojima, I.; Vidal, E. S. J. Org. Chem. 1998, 63, 7999.
34. Thompson, A. S.; Humphrey, G. R.; De Marco, A. M.; Mathre, D. J.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 5886.