Chiral lactols, XIV: Stereoselective fusion of five-membered ring lactols to the bornane ring system

Liebigs Annales

Volumn , Issue 6, 1996, Pages 1015-1021

  Noe, Christian R ^a   Knollmüller, Max ^b   Gärtner, Peter ^b   Mereiter, Kurt ^b   Steinbauer, Gerhard ^c  

^a GOETHE UNIVERSITY   (Germany)

^b VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^c Asota GesmbH   (Austria)

Author keywords

Lactols, fused; Reagents, stereoselective

Indexed keywords

EID: 0002417696     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960623     Document Type: Article

References (53)

1. C. R. Noe, Chem. Ber. 1982, 115, 1576-1590.
2. C. R. Noe, M. Knollmüller, G. Steinbauer, E. Jangg, H. Völlenkle, Chem. Ber. 1988, 121, 1231-1239.
3. [23]).
4. [4a] M. Knollmüller, C. R. Noe, B. Oberhauser, Monatsh. Chem. 1986, 117, 407-419.
5. [4b] C. R. Noe, M. Knollmüller, G. Göstl, B. Oberhauser, H. Völlenkle, Angew. Chem. 1987, 99, 467-470;
6. Angew. Chem. Im. Ed. Engl. 1987, 26, 442-444.
7. [4c] C. R. Noe, M. Knollmüller, P. Ettmayer, Angew. Chem. 1988, 100, 1431-1433;
8. Angew. Chem. Int. Ed. Engl. 1988, 27, 1379-1381.
9. [4d] C. R. Noe, M. Knollmüller, K. Dungler, C. Miculka, Chem. Ber. 1994, 127, 359-365.
10. C. R. Noe, M. Knollmüller, P. Ettmayer, P. Gärtner, M. Letschnig, Österr. Chem. Z. 1990, 36-41.
11. [6a] C. R. Noe, M. Knollmüller, K. Dungler, C. Miculka, P. Gärtner, Monatsh. Chem. 1991, 122, 705-718.
12. [6b] C. R. Noe, M. Knollmüller, P. Gärtner, W. Fleischhacker, E. Katikarides, Monatsh. Chem. 1995, 126, 481-494.
13. [6c] C. R. Noe, M. Knollmüller, P. Gärtner, W. Fleischhacker, E. Katikarides, Monatsh. Chem. 1995, 126, 557-564.
14. [6d] W. Lindner, Methods of Org. Chem. (Houben-Weyl) 4th ed. 1995, vol. E21a, p. 235.
15. [6d], p. 269-272.
16. [6f] G. Ecker, W. Fleischhacker, C. R. Noe, Arch. Pharm. (Weinheim, Ger.) 1994, 327, 691-695.
17. [7a] C. R. Noe, M. Knollmüller, H. Kürner, G. Steinbauer, H. Koberg, P. Gärtner, Monatsh. Chem. 1991, 122, 101-110.
18. [7b] C. R. Noe, M. Knollmüller, G. Steinbauer, E. Wagner, H. Kürner, P. Ettmayer, H. Völlenkle, Monatsh. Chem. 1991, 122, 299-317.
19. [7c] C. R. Noe, M. Knollmüller, G. Göstl, P. Gärtner, Monatsh. Chem. 1991, 122, 283-290.
20. [7d] M. Mäurer, H. B. Stegmann, Chem. Ber. 1990, 123, 1679-1685.
21. [7e] E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, p. 338.
22. [7f] F. Hammerschmidt, H. Völlenkle, Liebigs Ann. Chem. 1989, 577-583.
23. [7g] B. Hartmann, A. M. Kanazawa, J. P. Depres, A. E. Greene, Tetrahedron Lett. 1993, 34, 3875-3876.
24. [7h] Y. Zhou, P. Luan, L. A. Liu, Z. P. Sun, J. Chomatogr. - Biomedical Applications 1994, 659, 109-126.
25. [7i] R. W. Baker, S. O. Rea, M. V. Sargent, E. M. C. Schenkelaars, B. W. Skelton, A. H. White, Tetrahedron Asymmetry 1994, 5, 45-48.
26. [7j] K. Zimmermann, Monatsh. Chem. 1993, 124, 1157-1167.
27. [8a] C. R. Noe, M. Knollmüller, P. Ettmayer, Liebigs Ann. Chem. 1989, 637-643.
28. [8b] C. R. Noe, M. Knollmüller, P. Ettmayer, Liebigs Ann. Chem. 1991, 417-424.
29. [8c] W. Oppolzer, Tetrahedron 1987, 43, 1969-2004.
30. [9a] C. R. Noe, M. Knollmüller, C. Miculka, K. Dungler, E. Wagner, P. Ettmayer, Chem. Ber. 1994, 127, 887-892.
31. [9b] C. R. Noe, M. Knollmüller, P. Gärtner, E. Katikarides, L. Gaischin, H. Völlenkle, Liebigs Am. 1995, 1353-1360.
32. [11] and R. L. Halterman, K. P. C. Vollhardt, Tetrahedron Lett. 1986, 27, 1461-1464).
33. J. B. Tingle, J. Chem. Soc. 1890, 57, 652-655.
34. [11] it is stated that the yield is higher, if ether is used instead of toluene.
35. [13a] E. Vedejs in Org. React., vol. 22 (Ed.: W. G. Dauben), Wiley, New York, 1975, p. 401-422.
36. [13b] R. Mayer, H. Bürger, B. Matauschek, J. Prakt. Chem. 1961, 4, 261-268.
37. Under acidic conditions as maintained during the Clemmensen reduction, a mixture of 5 and 6 (60:40) afforded in equilibrium 5:6 = 83:17, which was approximately the same distribution as for the product isolated directly from the reduction step.
38. 40% is the yield of 8 as raw material, which can be used directly in the oxidation procedure.
39. R. V. Stevens, K. T. Chapman, H. N. Weller, J. Org. Chem. 1980, 45, 2030-2032.
40. If the content of 6 in 5 was 5%, the amount of 16 in 9 was about 10%. Since in the mother liquor of the crystallization process the best ratio of 9 to 16 was about 1:1, the total yield of isolated 9 was only about 40% (based on 5).
41. C. R. Noe, M. Knollmüller, E. Jangg, G. Steinbauer, Liebigs Ann. Chem. 1989, 645-650.
42. 1H-NMR data.
43. 12 can be purified by crystallization or chromatography, or the mixture of 12:13 = 7:3 is used for further synthesis without further purification.
44. 13C-NMR spectra of 14 (E) compared to 15 (Z) due to the γ effect.
45. If the content of 13 in 12 was 30%, the amount of 9 in 16 was about 15%. Since in the mother liquor of the crystallization process the best ratio of 16 to 9 was about 1:1, the total yield of isolated 16 was only about 50% (based on 12).
46. C. R. Noe, Chem. Ber. 1982, 115, 1591-1606.
47. Only in some special cases of kinetic investigations and in the formation of O,N-acetals were differences in the reactivity between lactols and lactol anhydrides observed.
48. [25l A further advantage of self-condensation is the possibility of removing easily small amounts of the wrong enantiomer since in the condensation step diastereomers are formed. Otherwise, the enantiomeric purity of the final product would be limited by the purity of camphor.
49. W. Langenbeck, G. Triem, Ber. Dtsch. Chem. Ges. 1936, 69, 248-250.
50. H. Rupe, M. Werder, H. Takagi, Helv. Chim. Acta 1918, 1, 325.
51. XTAL3.2, Integrated System of Computer Programs for Crystal Structure Determination (Eds.: S. R. Hall, H. D. Flack, J. M. Stewart), Univs. of Western Australia, Geneva and Maryland, 1992.
52. G. M. Sheldrick, SHELXL93, Program for Crystal Structure Refinement, University of Göttingen, 1993.
53. Further details of the crystal structure investigation are available from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen (Germany), on quoting the depository number CSD-59218.