Pentaspiranes and hexaspiranes with 1,3-dioxane or 1,3-oxathiane rings: Synthesis and stereochemistry

Tetrahedron

Volumn 60, Issue 14, 2004, Pages 3173-3189

  Terec, Anamaria ^a   Grosu, Ion ^a   Condamine, Eric ^b   Breau, Livain ^c   Plé, Gérard ^b   Ramondenc, Yvan ^b   Rochon, Fernande D ^c   Peulon Agasse, Valérie ^b   Opris, Dorina ^a  

^a BABE BOLYAI UNIVERSITY   (Romania)

^b UNIVERSITÉ DE ROUEN   (France)

^c UNIVERSITÉ DU QUÉBEC À MONTRÉAL   (Canada)

Author keywords

Conformational analysis; Helical and axial chirality; Polyspiranes

Indexed keywords

1,3 DIOXANE DERIVATIVE; 1,3 OXATHIANE DERIVATIVE; ALKANE DERIVATIVE; DISPIRO 1,3 OXATHIANE; TETRASPIRO 1,3 OXATHIANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 1642330134     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.02.027     Document Type: Article

References (41)

1. Grosu I., Mager S., Plé G., Horn M. J. Chem. Soc., Chem. Commun. 1995;167-168.
2. Grosu I., Mager S., Plé G. J. Chem. Soc., Perkin Trans. 2. 1995;1351-1357.
3. Grosu I., Mager S., Plé G., Mesaros E. Tetrahedron. 52:1996;12783-12798.
4. Opris D., Grosu I., Toupet L., Plé G., Terec A., Mager S., Muntean L. J. Chem. Soc., Perkin Trans. 1. 2001;2413-2420.
5. Grosu I., Mager S., Plé G., Martinez R. Chirality. 8:1996;311-315.
6. Terec A., Grosu I., Muntean L., Toupet L., Plé G., Socaci C., Mager S. Tetrahedron. 57:2001;8751-8758.
7. Greenberg A., Laszlo P. Tetrahedron Lett. 1970;2641-2644.
8. Mursakulov I.G., Ramazanov E.A., Guseinov M.M., Zefirov N.S., Samoshin V.V., Eliel E.L. Tetrahedron. 36:1980;1885-1890.
9. Dodziuk H. J. Chem. Soc., Perkin Trans. 2. 1986;249-252.
10. Dodziuk H., Sitkowski J., Stefanian I., Mursakulov I.G., Guseinov M.M., Kurbanova V.A. Struct. Chem. 3:1992;269-276.
11. Fitjer L., Klages U., Wehle D., Giersig M., Schormann N., Clegg W., Stephenson D.S., Binsch G. Tetrahedron. 44:1988;405-416.
12. Giersig M., Wehle D., Fitjer L., Schormann N., Clegg W. Chem. Ber. 121:1988;525-532.
13. Fitjer L., Kuehn W., Klages U., Egert E., Clegg W., Schormann N., Sheldrick G.M. Chem. Ber. 117:1984;3075-3092.
14. Fitjer L., Giersig M., Clegg W., Schormann N. Tetrahedron Lett. 24:1983;5351-5354.
15. Fitjer L., Wehle D., Noltemeyer J., Egert E., Sheldrick G.M. Chem. Ber. 117:1984;203-221.
16. de Meijere A., Kozhushkov S.I., von Seebach M., Boese R., Benet-Buchholz J., Yufit D.S., Howard J.A.K. Angew. Chem., Int. Ed. 39:2000;2495-2498.
17. Shizuma M., Kadoya Y., Takai Y., Imamura H., Yamada H., Takeda T., Arakawa R., Takahashi S., Sawada M. J. Org. Chem. 67:2002;4795-4807.
18. Rablen P.R., Paquette L.A., Borden W.T. J. Org. Chem. 65:2000;9180-9185.
19. de Meijere A., Kozhushkov S.I., Puls C., Haumann T., Boese R. Angew. Chem. 106:1994;934-936.
20. Wulf K., Klages U., Rissom B., Fitjer L. Tetrahedron. 53:1997;6011-6018.
21. Yufit D.S., Struchkov Y.T., Kozhushkov S.I., de Meijere A. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 49:1993;1517-1519.
22. Fitjer L., Justus K., Puder P., Dittmer M., Hassler C., Noltemeyer J. Angew. Chem. 103:1991;431-433.
23. de Meijere A., Jaekel F., Simon A., Borrmann H., Koehler J., Johnels D., Scott L.T. J. Am. Chem. Soc. 113:1991;3935-3941.
24. Fitjer L., Giersig M., Wehle D., Dittmer M., Koltermann G.-W., Schormann N., Egert E. Tetrahedron. 44:1988;393-404.
25. Fitjer L., Klages U., Kuehn W., Stephenson D.S., Binsch G., Noltemeyer J., Egert E., Sheldrick G.M. Tetrahedron. 40:1984;4337-4350.
26. Eliel E.L., Wilen S. Stereochemistry of organic compounds. 1994;Wiley, New York. p 1191.
27. Buchweller C.H. Juaristi E. Stereodynamics of cyclohexane and substituted cyclohexanes. Substituent A values in conformational behavior of six-membered ring. 1995;42 VCH, New York.
28. Friebolin H., Schmid H.G., Kabuss S., Faisst W. Org. Magn. Reson. 1:1969;67-86.
29. Pihlaja K., Pasanen P., Wähäsilta J. Org. Magn. Reson. 12:1979;331-336.
30. Pasanen P., Pihlaja K. Tetrahedron. 28:1972;2617-2626.
31. Siemens XSCANS, SHELXS-97, SHELXL-97 and Siemens SHELXTL programs.
32. Sheldrik, G. M. SHELX-97; Universität Göttingen, Germany, 1997.
33. Bruker. SMART (Version 5.611), SAINT (Version 6.02a), SHELXTL (Version 5.10) and SADABS; Bruker AXS Inc., Madison, Wisconsin, 1999. Claridge J.B., Layland R.C., zur Loye H.-C. Acta Crystallogr. Sect. C. 53:1997;1740.
34. Bruker. SMART (Version 5.611), SAINT (Version 6.02a), SHELXTL (Version 5.10) and SADABS; Bruker AXS Inc., Madison, Wisconsin, 1999. Claridge J.B., Layland R.C., zur Loye H.-C. Acta Crystallogr. Sect. C. 53:1997;1740.
35. Farrugia L.J. J. Appl. Crystallogr. 30:1997;565.
36. Terec, A. Ph.D. Thesis, Babes-Bolyai University, 2003.
37. Campbell T.W., Foldi V.S. J. Org. Chem. 26:1961;4654-4658.
38. Jung M.E., McCombs C.A. Org. Synth. 58:1979;163-164.
39. Rigby J.H., Kotnis A., Kramer J. J. Org. Chem. 55:1990;5078-5088.
40. Anteunis M., Geens A., van Cauwenberghe R. Bull. Soc. Chim. Belg. 82:1973;573-590.
41. Feuerbacher N., Vögtle F., Windscheidt J., Poetsch E., Nieger M. Synthesis. 1999;117-120.