Synthesis of both enantiomers of optically pure saturated and α,β-unsaturated γ-substituted γ-lactones from chiral sulphoxides. X-ray molecular structure of (3R,4S)-4-methyl-4-t-butyl-3-(p- tolylthio)butanolide and of (3R,4R)-4-(cyclohex-1-enyl)-4-methyl-3-(p-tolylthio) butanolide

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue , 1986, Pages 1405-1415

  Albinati, Alberto ^a   Bravo, Pierfrancesco ^a   Ganazzoli, Fabio ^a   Resnati, Giuseppe ^a   Viani, Fiorenza ^a  

^a POLITECNICO DI MILANO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013030399     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19860001405     Document Type: Article

References (74)

1. G. Ohloft, ‘Progress in the Chemistry of Organic Natural Products,’ Springer-Verlag, 1978, vol. 35
2. Tse-Lok Ho, Synth. Commun., 1983, 13, 341
3. L J. Gräfe, G. Reinhardt, W. Schade, D. Krebs, I. Eritt, W. F. Fleck, E. Heinrich, and J. Radies, J. Antibiot., 1982, 35, 609
4. J. R. Pougny, Tetrahedron Lett., 1984, 25, 2363
5. L. Stamatatos, P. Sinay, and J. R. Pougny, Tetrahedron, 1984, 40, 1713
6. J. M. Brand, J. C. Joung, and R. M. Silverste, ‘Progress in the Chemistry of Organic Natural Products,’ Springer-Verlag, 1979, vol. 37
7. R. Baker and V. B. Rao, J. Chem. Soc., Perkin Trans. 1, 1982, 69
8. R. G. Brownlee, R. M. Silverstein, D. Muller-Schwarze, and A. G. Singer, Nature, 1969, 221, 284
9. K. Mori, T. Ebata, and S. Takechi, Tetrahedron, 1984, 40, 1761
10. D. L. Wood, L. E. Browme, B. Ewig, K. Lindahl, W. D. Bedard, P. E. Tilden, K. Mori, G. B. Pitman, and P. R. Hughes, Science, 1976, 192, 896
11. L. Friedman and J. G. Miller, Science, 1971, 172, 1044
12. J. Cardellach, C. Estopa, J. Font, M. Moreno-Manas, R. M. Ortuiio, Sanches-Ferrando, S. Valle, and L. Vilamajo, Tetrahedron, 1982, 38, 2377
13. A. Numata, K. Hokimoto, T. Takemura, T. Katsuno, and K. Yamamoto, Chem. Pharm. Bull., 1984,32,2815
14. K. H. Hollenbeak and M. E. Kuehne, Tetrahedron, 1974, 30, 2307
15. S. K. Agarwal and R. P. Rastogi, Phytochemistry, 1978, 17, 1663
16. K. Tomioka, H. Kawasaki, Y. Iitaka, and K. Koga, Tetrahedron Lett., 1985,26,903
17. K. Tomioka, F. Sato, and K. Koga, Heterocycles, 1982, 17, 311
18. K. Tomioka, T. Ishiguro, and K. Koga, Tetrahedron Lett., 1980, 21, 2973
19. K. Tomioka, T. Ishiguro, and K. Koga J. Chem. Soc., Chem. Commun., 1979, 652
20. K. Tomioka, H. Mizuguchi, and K. Koga, Tetrahedron Lett., 1978, 4687
21. M. Taniguchi, K. Koga, and S. Yamada, Tetrahedron, 1974, 30, 3547
22. S. Takano, M. Yonoga, K. Chiba, and K. Ogasawara, Tetrahedron Lett., 1980, 21, 3697
23. J. P. Vigneron, R. Meric, M. Larchêveque, A. Debal, G. Kunesch, P. Zagatti, and M. Gallois, Tetrahedron Lett., 1982, 23, 5051
24. J. P. Vigneron, R. Meric, and M. Dhaenens, Tetrahedron Lett., 1980, 21, 2057
25. J. P. Vigneron, R. Meric, and M. Dhaenens Jpn. Kokai Tokkyo Koho JP 81 128 776/1981
26. J. P. Vigneron, R. Meric, and M. Dhaenens Chem. Abstr., 1982, 96, 85405r
27. J. P. Vigneron, R. Meric, and M. Dhaenens Jpn. Kokai Tokkyo Koho JP 81 65 883/1981
28. J. P. Vigneron, R. Meric, and M. Dhaenens Chem. Abstr., 1981, 95, 168872d
29. S. Takano, M. Yonaga, M. Marimoto, and K. Ogasawara, J. Chem. Soc., Perkin Trans. 1, 1985, 305
30. F. Toda, K. Tanaka, T. Omata, K. Nakamura, and T. Oshima, J. Am. Chem. Soc., 1983, 105, 5151
31. F. Toda, K. Tanaka, and H. Ueda, Tetrahedron Lett., 1981, 22, 4669
32. W. H. Pirkle and P. E. Adams, J. Org. Chem., 1979, 44, 2169
33. Pak-Tsun Ho and N. Davies, Synthesis, 1983, 462
34. S. Takano, M. Yonaga, and K. Ogasawara, Synthesis., 1981, 265
35. P. Camps, J. Font, and O. Ponsati, Tetrahedron Lett., 1981, 22, 1471
36. E. Klein, H. Farnow, and W. Rojann, Justus Liebigs Ann. Chem., 1964,675, 73
37. S. Musierowicz and A. E. Wroblewski, Tetrahedron, 1978, 34, 461
38. T. Mukaiyama and K. Suzuki, Chem. Lett., 1980, 255
39. M. M. Midland and N. H. Nguyen, J. Org. Chem., 1981, 46, 4107
40. M. Nishizawa, M. Yamada, and R. Noyori, Tetrahedron Lett., 1981, 22, 247
41. M. M. Midland and A. Tramontano, Tetrahedron Lett., 1980, 21, 3549
42. J. P. Vigneron and J. M. Blanchard, Tetrahedron Lett., p. 1739
43. J. P. Vigneron and V. Bloy, Tetrahedron Lett. 1735
44. P. Brownbridge, E. Egert, P. G. Hunt, O. Kennard, and S. Warren, J. Chem. Soc., Perkin Trans. 1,1981,2751 and references cited therein
45. G. H. Posner, T. P. Kogan, S. R. Haines, and L. L. Frye, Tetrahedron Lett., 1984, 25, 2627
46. G. Solladie and F. Matloubi-Moghadam, J. Org. Chem., 1982,47,91
47. D. Seebach, Angew. Chem., 1979, 91, 259
48. D. Seebach Angew. Chem., Int. Ed. Engl., 1979, 18, 239
49. P. Bravo, P. Carrera, G. Resnati, and C. Ticozzi, Chem. Commun., 1984,19
50. P. Bravo, P. Carrera, and G. Resnati, Fifth International Conference on Organic Synthesis, Freiburg, August, 1984, M10, 48
51. C. J. Harris, Tetrahedron Lett., 1981, 22, 4863
52. O. P. Vig, J. C. Kapur, and S. D. Sharma, J. Indian Chem. Soc., 1968, 734
53. P. Bravo and G. Resnati, Tetrahedron Lett., 1985, 26, 5601
54. P. Bravo, G. Resnati, and F. Viani, Tetrahedron Lett., 1985, 26, 2913
55. T. Durst, R. Viau, and M. R. McClory, J. Am. Chem. Soc., 1971, 93, 3077
56. J. F. Biellmann and J. J. Vicens, Tetrahedron Lett, 1974, 2915
57. J. F. Biellmann J. J. Vicens Tetrahedron Lett., 1978, 467.
58. B. M. Trost, H. C. Arndt, P. E. Strege, and R. Verhoeven Tetrahedron Lett., 1976, 3477
59. P. A. Barlett, J. Am. Chem. Soc., 1976, 98, 3305
60. J. Drabowicz and S. Oae, Synthesis, 1977, 404
61. P. Vlad and M. Soucek, Collect. Czech. Chem. Commun., 1962, 27, 1726
62. E. Demole and D. Berthet, Helv. Chim. Acta, 1972, 55, 1866
63. I. Uchida and K. Kuriyama, Tetrahedron Lett, 1974, 3761
64. D. R. Williams, J. G. Phillips, and J. C. Huffman J. Org. Chem 1981, 4101
65. C. H. Heathcock, C. T. Vite, J. J. Morrison, and D. Van Derweer, J. Org. Chem., 1981, 46, 1296
66. P. Main, L. Lessinger, M. M. Woolfson, G. Germain, and J. P. Declerq, MULTAN 76. A System of Computer Programs for the Automatic Solution of Crystal Structures from X-Ray Diffraction Data,’ Universities of York, England, and Louvain, Belgium
67. G. Sheldrick, ‘SHELX. A Program for X-Ray Crystal Structure Determination,’ 1976, University of Cambridge, England
68. International Tables for X-Ray Crystallography, Kynoch Press, Birmingham, 1974, vol. 4
69. W. C. Hamilton, Acta Crystallogr., 1965, 18, 502
70. C. K. Johnson, ‘ORTEP, 1965. Report ORNL-3794.’ Oak Ridge National Laboratory, Tennessee
71. A. Gieren. P. Narayanan, W. Hoppe, M. Hasan, K. Michl, T. Wieland, H. O. Smith, G. Joung, and E. Breitmaier, Justus Liebigs Ann. Chem., 1974, 1561
72. E. Benedetti, P. Ganis, G. Bombieri, L. Caglioti, and G. Germain, Acta Crystallogr., Sect. B, 1975, 31, 1097
73. R. F. Bryan and M.-S. Shen, Acta Crystallogr., 1978,34, 327
74. G. Bocelli and M. F. Grenier-Loustalot J. Chem. Res. (S), 1980, 227