Pigments of fungi. XLIV* synthesis of differentially protected chiral pentane-1,3,5-triol derivatives; confirmation of the absolute configuration of naturally occurring 3-acetoxy-2,3-dihydropiptoporic acid

Australian Journal of Chemistry

Volumn 50, Issue 11, 1997, Pages 1067-1079

  Burns, Christopher J ^a,b   Gill, Melvyn ^a   Saubern, Simon ^a,c  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

^c CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001284480     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/C97111     Document Type: Article

References (49)

1. Gill, M., J. Chem. Soc., Perkin Trans. 1, 1982, 1449.
2. Serck-Hanssen, K., Ark. Kemi, 1955, 10, 135.
3. Brooks, D. W., and Palmer, J. T., Tetrahedron Lett., 1983, 24, 3059.
4. Morrison, M. A., and Miller, M. J., J. Org. Chem., 1983, 48, 4421.
5. Ohno, M., Kobayashi, S., Iimori, T., Wang, Y. F., and Izawa, T., J. Am. Chem. Soc., 1981, 103, 2405.
6. Herold, P., Mohr, P., and Tamm, C., Helv. Chim. Acta, 1983, 66, 744.
7. Rosen, T., Watanabe, M., and Heathcock, C. H., J. Org. Chem., 1984, 49, 3657.
8. Cohen, S. G., and Khedouri, E., J. Am. Chem. Soc., 1961, 83, 4228.
9. Mohr, P., Rösslein, L., and Tamm, Ch., Helv. Chim. Acta, 1987, 70, 142.
10. Mohr, P., Waespe-Sarcevic, N., Tamm, Ch., Gawronska, K., and Gawronski, J. K., Helv. Chim. Acta, 1983, 66, 2501.
11. Roy, R., and Rey, A. W., Tetrahedron Lett., 1987, 28, 4935.
12. Monteiro, J., Braun, J., and Le Goffic, F., Synth. Commun., 1990, 20, 315.
13. Carlson, R. G., and Henton, D. E., J. Chem. Soc., Chem. Commun., 1969, 674.
14. Evans, D. A., and Nelson, J. V., J. Am. Chem. Soc., 1980, 102, 774.
15. For example, see: Murray, T. F., Varma, V., and Norton, J. R., J. Chem. Soc., Chem. Commun., 1976, 907; Fried, J., Lin, C.-H., and Ford, S. H., Tetrahedron Lett., 1969, 10, 1379.
16. For example, see: Murray, T. F., Varma, V., and Norton, J. R., J. Chem. Soc., Chem. Commun., 1976, 907; Fried, J., Lin, C.-H., and Ford, S. H., Tetrahedron Lett., 1969, 10, 1379.
17. Still, W. C., and Ohmizu, H., J. Org. Chem., 1981, 46, 5242.
18. Johnson, W. S., Jensen, N. P., Hooz, J., and Leopold, E. J., J. Am. Chem. Soc., 1968, 90, 5872.
19. For example, see: Bus, J., and Frost, D. J., Recl Trav. Chim. Pays-Bas, 1974, 93, 213.
20. Grant, B., and Djerassi, C., J. Org. Chem., 1974, 39, 968.
21. Nicolaou, K. C., and Ahn, K. H., Tetrahedron Lett., 1989, 30, 1217.
22. Kotecha, N. R., Ley, S. V., and Mantegani, S., Synlett, 1992, 395.
23. Gao, Y., Hanson, R. M., Klunder, J. M., Ko, S. Y., Masamune, H., and Sharpless, K. B., J. Am. Chem. Soc., 1987, 109, 5765.
24. Kozikowski, A. P., and Stein, P. D., J. Org. Chem., 1984, 49, 2301.
25. Trost, B. M., Belletire, J. E., Godleski, S., McDougal, P. G., Balkovec, J. M., Baldwin, J. J., Christy, M. E., Ponticello, G. S., Varga, S. L., and Springer, J. P., J. Org. Chem., 1986, 51, 2370.
26. Finan, J. M., and Kishi, Y., Tetrahedron Lett., 1982, 23, 2719.
27. Corey, E. J., and Venkateswarlu, A., J. Am. Chem. Soc., 1972, 94, 6190.
28. Steglich, W., and Höfle, G., Angew. Chem., Int. Ed. Engl., 1969, 8, 981.
29. Greene, T. W., (Ed.) 'Protecting Groups in Organic Synthesis' (a) p. 44; (b) p. 296, 1st Edn (Wiley-Interscience: New York 1980).
30. Greene, T. W., (Ed.) 'Protecting Groups in Organic Synthesis' (a) p. 44; (b) p. 296, 1st Edn (Wiley-Interscience: New York 1980).
31. Franke, F., and Gutherie, R. D., Aust. J. Chem., 1978, 31, 1285.
32. Stork, G., and Takahashi, T., J. Am. Chem. Soc., 1977, 99, 1275.
33. Gill, M., and Smrdel, A. F., Tetrahedron: Asymmetry, 1990, 1, 453.
34. Gorey, E. J., and Schmidt, G., Tetrahedron Lett., 1980, 21, 731.
35. Carlsen, P. H. J., Katsuki, T., Martín, V. S., and Sharpless, K. B., J. Org. Chem., 1981, 46, 3938.
36. Bieg, T., and Szesa, W., Synthesis, 1985, 77.
37. Anantharamaiah, G. M., and Sivanandaiah, V. M., J. Chem. Soc., Perkin Trans. 1, 1977, 490.
38. Hanessian, S., Liak, T. J., and Vanasse, B., Synthesis, 1981, 396.
39. Fuji, K., Ichikawa, K., Node, M., and Fujita, E., J. Org. Chem., 1979, 44, 1661.
40. Brinkley, R. W., and Hehemann, D. G., J. Org. Chem., 1990, 55, 378.
41. Mori, K., and Seu, Y.-B., Tetrahedron, 1988, 44, 1035.
42. Hanessian, S., Delorme, D., and Dufresne, Y., Tetrahedron Lett., 1984, 25, 2515.
43. Derome, A. E., (Ed.) 'Modern NMR Techniques for Chemistry Research' (Pergamon: Oxford 1989); Martin, G. E., and Zektzer, A. S., 'Two-Dimensional NMR Methods for Establishing Molecular Connectivity' (VCH: New York 1988).
44. Derome, A. E., (Ed.) 'Modern NMR Techniques for Chemistry Research' (Pergamon: Oxford 1989); Martin, G. E., and Zektzer, A. S., 'Two-Dimensional NMR Methods for Establishing Molecular Connectivity' (VCH: New York 1988).
45. Burfield, D. R., and Smithers, R. H., J. Org. Chem., 1983, 48, 2420, and references cited therein.
46. Perrin, D. D., and Armarego, W. L. F., 'Purification of Laboratory Chemicals' 3rd Edn (Pergamon: Oxford 1988).
47. Still, W. C., Kahn, M., and Mitra, A., J. Org. Chem., 1978, 43, 2923.
48. Jones, M. G., and Mann, M. J., J. Am. Chem. Soc., 1953, 75, 4048.
49. Bohlmann, F., Ganzer, M., Krüger, M., and Nordhoff, E., Tetrahedron, 1983, 39, 123.