Enantiomerically pure Diels-Alder adducts of maleic anhydride to furfural acetals through thermodynamic control. Single crystal and molecular structure of (1S,4R,4'S,5'S)-1-(4',5'-dimethyldioxolan-2'-yl)-5,6-dimethylidene-7-o xabicyclo[2.2.1]hept-2-ene

Tetrahedron Asymmetry

Volumn 7, Issue 11, 1996, Pages 3153-3162

  Guidi, Antonio ^a,c   Theurillat Moritz, Viviane ^a   Vogel, Pierre ^a   Pinkerton, A Alan ^b  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b UNIVERSITY OF TOLEDO   (United States)

^c Dept of Pharmacology   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNANE DERIVATIVE;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; CRYSTALLOGRAPHY; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS; X RAY DIFFRACTION;

EID: 0030575814     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00417-X     Document Type: Article

References (95)

1. 1. For reviews, see e.g.: a) Lipschutz, B. H. Chem. Rev. 1986, 86, 795;
2. b) Vogel, P.; Auberson, Y.; Bimwala, M.; de Guchteneere, E.; Vieira, E.; Wagner, J. in "Trends in Synthetic Carbohydrate Chemistry", Horton, D.; Hawkins, L. D.; McGarvey, G. J., Eds., ACS Symposium Series 386; American Chemical Society: Washington, D. C. 1989, p. 197;
3. c) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173;
4. d) Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395;
5. e) Shipman, M. Contemporary Organic Synthesis, 1995, 2, 1.
6. 2. See e.g.: Adams, R.; Voorhees, V. Org. Synth. Coll. Vol. I. J. Wiley & Sons., New York, 1932, p. 274; McKillip, W. J.; Sherman, E. "KIRK OTMER Encyclopedia of Chemical Technology", J. Wiley & Sons, New York, Grayston, M.; Eckroth, D. Eds.; 1980, Vol. 11, p. 499-527.
7. 2. See e.g.: Adams, R.; Voorhees, V. Org. Synth. Coll. Vol. I. J. Wiley & Sons., New York, 1932, p. 274; McKillip, W. J.; Sherman, E. "KIRK OTMER Encyclopedia of Chemical Technology", J. Wiley & Sons, New York, Grayston, M.; Eckroth, D. Eds.; 1980, Vol. 11, p. 499-527.
8. 3. See e.g.: Diels, O.; Alder, K. Ber. 1929, 62, 554; Lee, M. W.; Herndon, W. C. J. Org. Chem. 1978, 43, 518; Dauben, W. G.; Lam, J. Y. L.; Guo, Z. R. Ibid. 1996, 61, 4816.
9. 3. See e.g.: Diels, O.; Alder, K. Ber. 1929, 62, 554; Lee, M. W.; Herndon, W. C. J. Org. Chem. 1978, 43, 518; Dauben, W. G.; Lam, J. Y. L.; Guo, Z. R. Ibid. 1996, 61, 4816.
10. 3. See e.g.: Diels, O.; Alder, K. Ber. 1929, 62, 554; Lee, M. W.; Herndon, W. C. J. Org. Chem. 1978, 43, 518; Dauben, W. G.; Lam, J. Y. L.; Guo, Z. R. Ibid. 1996, 61, 4816.
11. 4. a) Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979;
12. b) Black, K. A.; Vogel, P. Helv. Chim. Acta 1984, 67, 1612; Ogawa, S.; Iwasawa, Y.; Nose, T.; Suami, T.; Ohba, S.; Ito, M.; Saito, Y. J. Chem. Soc., Perkin Trans. I 1985, 903; Grieco, P. A.; Lis, R.; Zelle, R. E.; Finn, J. J. Am. Chem. Soc. 1986, 108, 5908; Ferrari, T.; Vogel, P. Tetrahedron Lett. 1986, 27, 5507; Warm, A.; Vogel, P. Helv. Chim. Acta 1987, 70, 690; Wagner, J.; Vieira, E.; Vogel, P. Ibid. 1988, 71, 624.
13. b) Black, K. A.; Vogel, P. Helv. Chim. Acta 1984, 67, 1612; Ogawa, S.; Iwasawa, Y.; Nose, T.; Suami, T.; Ohba, S.; Ito, M.; Saito, Y. J. Chem. Soc., Perkin Trans. I 1985, 903; Grieco, P. A.; Lis, R.; Zelle, R. E.; Finn, J. J. Am. Chem. Soc. 1986, 108, 5908; Ferrari, T.; Vogel, P. Tetrahedron Lett. 1986, 27, 5507; Warm, A.; Vogel, P. Helv. Chim. Acta 1987, 70, 690; Wagner, J.; Vieira, E.; Vogel, P. Ibid. 1988, 71, 624.
14. b) Black, K. A.; Vogel, P. Helv. Chim. Acta 1984, 67, 1612; Ogawa, S.; Iwasawa, Y.; Nose, T.; Suami, T.; Ohba, S.; Ito, M.; Saito, Y. J. Chem. Soc., Perkin Trans. I 1985, 903; Grieco, P. A.; Lis, R.; Zelle, R. E.; Finn, J. J. Am. Chem. Soc. 1986, 108, 5908; Ferrari, T.; Vogel, P. Tetrahedron Lett. 1986, 27, 5507; Warm, A.; Vogel, P. Helv. Chim. Acta 1987, 70, 690; Wagner, J.; Vieira, E.; Vogel, P. Ibid. 1988, 71, 624.
15. b) Black, K. A.; Vogel, P. Helv. Chim. Acta 1984, 67, 1612; Ogawa, S.; Iwasawa, Y.; Nose, T.; Suami, T.; Ohba, S.; Ito, M.; Saito, Y. J. Chem. Soc., Perkin Trans. I 1985, 903; Grieco, P. A.; Lis, R.; Zelle, R. E.; Finn, J. J. Am. Chem. Soc. 1986, 108, 5908; Ferrari, T.; Vogel, P. Tetrahedron Lett. 1986, 27, 5507; Warm, A.; Vogel, P. Helv. Chim. Acta 1987, 70, 690; Wagner, J.; Vieira, E.; Vogel, P. Ibid. 1988, 71, 624.
16. b) Black, K. A.; Vogel, P. Helv. Chim. Acta 1984, 67, 1612; Ogawa, S.; Iwasawa, Y.; Nose, T.; Suami, T.; Ohba, S.; Ito, M.; Saito, Y. J. Chem. Soc., Perkin Trans. I 1985, 903; Grieco, P. A.; Lis, R.; Zelle, R. E.; Finn, J. J. Am. Chem. Soc. 1986, 108, 5908; Ferrari, T.; Vogel, P. Tetrahedron Lett. 1986, 27, 5507; Warm, A.; Vogel, P. Helv. Chim. Acta 1987, 70, 690; Wagner, J.; Vieira, E.; Vogel, P. Ibid. 1988, 71, 624.
17. b) Black, K. A.; Vogel, P. Helv. Chim. Acta 1984, 67, 1612; Ogawa, S.; Iwasawa, Y.; Nose, T.; Suami, T.; Ohba, S.; Ito, M.; Saito, Y. J. Chem. Soc., Perkin Trans. I 1985, 903; Grieco, P. A.; Lis, R.; Zelle, R. E.; Finn, J. J. Am. Chem. Soc. 1986, 108, 5908; Ferrari, T.; Vogel, P. Tetrahedron Lett. 1986, 27, 5507; Warm, A.; Vogel, P. Helv. Chim. Acta 1987, 70, 690; Wagner, J.; Vieira, E.; Vogel, P. Ibid. 1988, 71, 624.
18. 5. Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389.
19. 6. Das, J.; Haslanger, M. F.; Gougoutas, J. Z.; Malley, M. F. Synthesis 1987, 1100; Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 4120; Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167; Real, S. D.; Kronenthal, D. R.; Wu, H. Y. Ibid. 1993, 34, 8063; Dienes, Z.; Antonsson, T.; Vogel, P. Ibid. 1993, 34, 1013; Seebach, D.; Jaeschke, G.; Ming Wang, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 2395; For the asymmetric hydroxylation of 7-oxabicyclo[2.2.1]hept-2-ene derivatives, see: Brown, H. C.; Prasad, J. V. N. V. J. Am. Chem. Soc. 1986, 108, 2049; Hayashi, T. J. Synth. Org. Chem. Jpn. 1994, 52, 900; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335.
20. 6. Das, J.; Haslanger, M. F.; Gougoutas, J. Z.; Malley, M. F. Synthesis 1987, 1100; Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 4120; Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167; Real, S. D.; Kronenthal, D. R.; Wu, H. Y. Ibid. 1993, 34, 8063; Dienes, Z.; Antonsson, T.; Vogel, P. Ibid. 1993, 34, 1013; Seebach, D.; Jaeschke, G.; Ming Wang, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 2395; For the asymmetric hydroxylation of 7-oxabicyclo[2.2.1]hept-2-ene derivatives, see: Brown, H. C.; Prasad, J. V. N. V. J. Am. Chem. Soc. 1986, 108, 2049; Hayashi, T. J. Synth. Org. Chem. Jpn. 1994, 52, 900; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335.
21. 6. Das, J.; Haslanger, M. F.; Gougoutas, J. Z.; Malley, M. F. Synthesis 1987, 1100; Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 4120; Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167; Real, S. D.; Kronenthal, D. R.; Wu, H. Y. Ibid. 1993, 34, 8063; Dienes, Z.; Antonsson, T.; Vogel, P. Ibid. 1993, 34, 1013; Seebach, D.; Jaeschke, G.; Ming Wang, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 2395; For the asymmetric hydroxylation of 7-oxabicyclo[2.2.1]hept-2-ene derivatives, see: Brown, H. C.; Prasad, J. V. N. V. J. Am. Chem. Soc. 1986, 108, 2049; Hayashi, T. J. Synth. Org. Chem. Jpn. 1994, 52, 900; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335.
22. 6. Das, J.; Haslanger, M. F.; Gougoutas, J. Z.; Malley, M. F. Synthesis 1987, 1100; Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 4120; Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167; Real, S. D.; Kronenthal, D. R.; Wu, H. Y. Ibid. 1993, 34, 8063; Dienes, Z.; Antonsson, T.; Vogel, P. Ibid. 1993, 34, 1013; Seebach, D.; Jaeschke, G.; Ming Wang, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 2395; For the asymmetric hydroxylation of 7-oxabicyclo[2.2.1]hept-2-ene derivatives, see: Brown, H. C.; Prasad, J. V. N. V. J. Am. Chem. Soc. 1986, 108, 2049; Hayashi, T. J. Synth. Org. Chem. Jpn. 1994, 52, 900; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335.
23. 6. Das, J.; Haslanger, M. F.; Gougoutas, J. Z.; Malley, M. F. Synthesis 1987, 1100; Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 4120; Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167; Real, S. D.; Kronenthal, D. R.; Wu, H. Y. Ibid. 1993, 34, 8063; Dienes, Z.; Antonsson, T.; Vogel, P. Ibid. 1993, 34, 1013; Seebach, D.; Jaeschke, G.; Ming Wang, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 2395; For the asymmetric hydroxylation of 7-oxabicyclo[2.2.1]hept-2-ene derivatives, see: Brown, H. C.; Prasad, J. V. N. V. J. Am. Chem. Soc. 1986, 108, 2049; Hayashi, T. J. Synth. Org. Chem. Jpn. 1994, 52, 900; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335.
24. 6. Das, J.; Haslanger, M. F.; Gougoutas, J. Z.; Malley, M. F. Synthesis 1987, 1100; Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 4120; Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167; Real, S. D.; Kronenthal, D. R.; Wu, H. Y. Ibid. 1993, 34, 8063; Dienes, Z.; Antonsson, T.; Vogel, P. Ibid. 1993, 34, 1013; Seebach, D.; Jaeschke, G.; Ming Wang, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 2395; For the asymmetric hydroxylation of 7-oxabicyclo[2.2.1]hept-2-ene derivatives, see: Brown, H. C.; Prasad, J. V. N. V. J. Am. Chem. Soc. 1986, 108, 2049; Hayashi, T. J. Synth. Org. Chem. Jpn. 1994, 52, 900; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335.
25. 6. Das, J.; Haslanger, M. F.; Gougoutas, J. Z.; Malley, M. F. Synthesis 1987, 1100; Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 4120; Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167; Real, S. D.; Kronenthal, D. R.; Wu, H. Y. Ibid. 1993, 34, 8063; Dienes, Z.; Antonsson, T.; Vogel, P. Ibid. 1993, 34, 1013; Seebach, D.; Jaeschke, G.; Ming Wang, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 2395; For the asymmetric hydroxylation of 7-oxabicyclo[2.2.1]hept-2-ene derivatives, see: Brown, H. C.; Prasad, J. V. N. V. J. Am. Chem. Soc. 1986, 108, 2049; Hayashi, T. J. Synth. Org. Chem. Jpn. 1994, 52, 900; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335.
26. 6. Das, J.; Haslanger, M. F.; Gougoutas, J. Z.; Malley, M. F. Synthesis 1987, 1100; Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 4120; Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167; Real, S. D.; Kronenthal, D. R.; Wu, H. Y. Ibid. 1993, 34, 8063; Dienes, Z.; Antonsson, T.; Vogel, P. Ibid. 1993, 34, 1013; Seebach, D.; Jaeschke, G.; Ming Wang, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 2395; For the asymmetric hydroxylation of 7-oxabicyclo[2.2.1]hept-2-ene derivatives, see: Brown, H. C.; Prasad, J. V. N. V. J. Am. Chem. Soc. 1986, 108, 2049; Hayashi, T. J. Synth. Org. Chem. Jpn. 1994, 52, 900; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335.
27. 6. Das, J.; Haslanger, M. F.; Gougoutas, J. Z.; Malley, M. F. Synthesis 1987, 1100; Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 4120; Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167; Real, S. D.; Kronenthal, D. R.; Wu, H. Y. Ibid. 1993, 34, 8063; Dienes, Z.; Antonsson, T.; Vogel, P. Ibid. 1993, 34, 1013; Seebach, D.; Jaeschke, G.; Ming Wang, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 2395; For the asymmetric hydroxylation of 7-oxabicyclo[2.2.1]hept-2-ene derivatives, see: Brown, H. C.; Prasad, J. V. N. V. J. Am. Chem. Soc. 1986, 108, 2049; Hayashi, T. J. Synth. Org. Chem. Jpn. 1994, 52, 900; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335.
28. 7. Ito, Y.; Shibata, T.; Arita, M.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 6739; Ohno, M.; Ito, Y.; Arita, M.; Shibata, T.; Adachi, K.; Sawai, H. Tetrahedron 1984, 40, 145; Jones, J. B.; Francis, C. J. Can. J. Chem. 1984, 62, 2578; Jones, J. B. Tetrahedron 1986, 42, 3351; Bloch, R.; Guibe-Jampel, E.; Girard, C. Tetrahedron Lett. 1985, 26, 4087; Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659; Lok, K. P.; Jakovac, J.; Jones, J. B. Ibid. 1985, 107, 2521; Asensio, G.; Andreu, C.; Marco, J. A. Chem. Ber. 1992, 125, 2233; Cinquin, C.; Schaper, I.; Mandville, G.; Bloch, R. Synlett 1995, 339; Andreu, C.; Marco, J. A.; Asensio, G. J. Chem. Soc., Perkin Trans. I 1990, 3209.
29. 7. Ito, Y.; Shibata, T.; Arita, M.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 6739; Ohno, M.; Ito, Y.; Arita, M.; Shibata, T.; Adachi, K.; Sawai, H. Tetrahedron 1984, 40, 145; Jones, J. B.; Francis, C. J. Can. J. Chem. 1984, 62, 2578; Jones, J. B. Tetrahedron 1986, 42, 3351; Bloch, R.; Guibe-Jampel, E.; Girard, C. Tetrahedron Lett. 1985, 26, 4087; Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659; Lok, K. P.; Jakovac, J.; Jones, J. B. Ibid. 1985, 107, 2521; Asensio, G.; Andreu, C.; Marco, J. A. Chem. Ber. 1992, 125, 2233; Cinquin, C.; Schaper, I.; Mandville, G.; Bloch, R. Synlett 1995, 339; Andreu, C.; Marco, J. A.; Asensio, G. J. Chem. Soc., Perkin Trans. I 1990, 3209.
30. 7. Ito, Y.; Shibata, T.; Arita, M.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 6739; Ohno, M.; Ito, Y.; Arita, M.; Shibata, T.; Adachi, K.; Sawai, H. Tetrahedron 1984, 40, 145; Jones, J. B.; Francis, C. J. Can. J. Chem. 1984, 62, 2578; Jones, J. B. Tetrahedron 1986, 42, 3351; Bloch, R.; Guibe-Jampel, E.; Girard, C. Tetrahedron Lett. 1985, 26, 4087; Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659; Lok, K. P.; Jakovac, J.; Jones, J. B. Ibid. 1985, 107, 2521; Asensio, G.; Andreu, C.; Marco, J. A. Chem. Ber. 1992, 125, 2233; Cinquin, C.; Schaper, I.; Mandville, G.; Bloch, R. Synlett 1995, 339; Andreu, C.; Marco, J. A.; Asensio, G. J. Chem. Soc., Perkin Trans. I 1990, 3209.
31. 7. Ito, Y.; Shibata, T.; Arita, M.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 6739; Ohno, M.; Ito, Y.; Arita, M.; Shibata, T.; Adachi, K.; Sawai, H. Tetrahedron 1984, 40, 145; Jones, J. B.; Francis, C. J. Can. J. Chem. 1984, 62, 2578; Jones, J. B. Tetrahedron 1986, 42, 3351; Bloch, R.; Guibe-Jampel, E.; Girard, C. Tetrahedron Lett. 1985, 26, 4087; Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659; Lok, K. P.; Jakovac, J.; Jones, J. B. Ibid. 1985, 107, 2521; Asensio, G.; Andreu, C.; Marco, J. A. Chem. Ber. 1992, 125, 2233; Cinquin, C.; Schaper, I.; Mandville, G.; Bloch, R. Synlett 1995, 339; Andreu, C.; Marco, J. A.; Asensio, G. J. Chem. Soc., Perkin Trans. I 1990, 3209.
32. 7. Ito, Y.; Shibata, T.; Arita, M.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 6739; Ohno, M.; Ito, Y.; Arita, M.; Shibata, T.; Adachi, K.; Sawai, H. Tetrahedron 1984, 40, 145; Jones, J. B.; Francis, C. J. Can. J. Chem. 1984, 62, 2578; Jones, J. B. Tetrahedron 1986, 42, 3351; Bloch, R.; Guibe-Jampel, E.; Girard, C. Tetrahedron Lett. 1985, 26, 4087; Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659; Lok, K. P.; Jakovac, J.; Jones, J. B. Ibid. 1985, 107, 2521; Asensio, G.; Andreu, C.; Marco, J. A. Chem. Ber. 1992, 125, 2233; Cinquin, C.; Schaper, I.; Mandville, G.; Bloch, R. Synlett 1995, 339; Andreu, C.; Marco, J. A.; Asensio, G. J. Chem. Soc., Perkin Trans. I 1990, 3209.
33. 7. Ito, Y.; Shibata, T.; Arita, M.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 6739; Ohno, M.; Ito, Y.; Arita, M.; Shibata, T.; Adachi, K.; Sawai, H. Tetrahedron 1984, 40, 145; Jones, J. B.; Francis, C. J. Can. J. Chem. 1984, 62, 2578; Jones, J. B. Tetrahedron 1986, 42, 3351; Bloch, R.; Guibe-Jampel, E.; Girard, C. Tetrahedron Lett. 1985, 26, 4087; Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659; Lok, K. P.; Jakovac, J.; Jones, J. B. Ibid. 1985, 107, 2521; Asensio, G.; Andreu, C.; Marco, J. A. Chem. Ber. 1992, 125, 2233; Cinquin, C.; Schaper, I.; Mandville, G.; Bloch, R. Synlett 1995, 339; Andreu, C.; Marco, J. A.; Asensio, G. J. Chem. Soc., Perkin Trans. I 1990, 3209.
34. 7. Ito, Y.; Shibata, T.; Arita, M.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 6739; Ohno, M.; Ito, Y.; Arita, M.; Shibata, T.; Adachi, K.; Sawai, H. Tetrahedron 1984, 40, 145; Jones, J. B.; Francis, C. J. Can. J. Chem. 1984, 62, 2578; Jones, J. B. Tetrahedron 1986, 42, 3351; Bloch, R.; Guibe-Jampel, E.; Girard, C. Tetrahedron Lett. 1985, 26, 4087; Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659; Lok, K. P.; Jakovac, J.; Jones, J. B. Ibid. 1985, 107, 2521; Asensio, G.; Andreu, C.; Marco, J. A. Chem. Ber. 1992, 125, 2233; Cinquin, C.; Schaper, I.; Mandville, G.; Bloch, R. Synlett 1995, 339; Andreu, C.; Marco, J. A.; Asensio, G. J. Chem. Soc., Perkin Trans. I 1990, 3209.
35. 7. Ito, Y.; Shibata, T.; Arita, M.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 6739; Ohno, M.; Ito, Y.; Arita, M.; Shibata, T.; Adachi, K.; Sawai, H. Tetrahedron 1984, 40, 145; Jones, J. B.; Francis, C. J. Can. J. Chem. 1984, 62, 2578; Jones, J. B. Tetrahedron 1986, 42, 3351; Bloch, R.; Guibe-Jampel, E.; Girard, C. Tetrahedron Lett. 1985, 26, 4087; Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659; Lok, K. P.; Jakovac, J.; Jones, J. B. Ibid. 1985, 107, 2521; Asensio, G.; Andreu, C.; Marco, J. A. Chem. Ber. 1992, 125, 2233; Cinquin, C.; Schaper, I.; Mandville, G.; Bloch, R. Synlett 1995, 339; Andreu, C.; Marco, J. A.; Asensio, G. J. Chem. Soc., Perkin Trans. I 1990, 3209.
36. 7. Ito, Y.; Shibata, T.; Arita, M.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 6739; Ohno, M.; Ito, Y.; Arita, M.; Shibata, T.; Adachi, K.; Sawai, H. Tetrahedron 1984, 40, 145; Jones, J. B.; Francis, C. J. Can. J. Chem. 1984, 62, 2578; Jones, J. B. Tetrahedron 1986, 42, 3351; Bloch, R.; Guibe-Jampel, E.; Girard, C. Tetrahedron Lett. 1985, 26, 4087; Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659; Lok, K. P.; Jakovac, J.; Jones, J. B. Ibid. 1985, 107, 2521; Asensio, G.; Andreu, C.; Marco, J. A. Chem. Ber. 1992, 125, 2233; Cinquin, C.; Schaper, I.; Mandville, G.; Bloch, R. Synlett 1995, 339; Andreu, C.; Marco, J. A.; Asensio, G. J. Chem. Soc., Perkin Trans. I 1990, 3209.
37. 7. Ito, Y.; Shibata, T.; Arita, M.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 6739; Ohno, M.; Ito, Y.; Arita, M.; Shibata, T.; Adachi, K.; Sawai, H. Tetrahedron 1984, 40, 145; Jones, J. B.; Francis, C. J. Can. J. Chem. 1984, 62, 2578; Jones, J. B. Tetrahedron 1986, 42, 3351; Bloch, R.; Guibe-Jampel, E.; Girard, C. Tetrahedron Lett. 1985, 26, 4087; Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659; Lok, K. P.; Jakovac, J.; Jones, J. B. Ibid. 1985, 107, 2521; Asensio, G.; Andreu, C.; Marco, J. A. Chem. Ber. 1992, 125, 2233; Cinquin, C.; Schaper, I.; Mandville, G.; Bloch, R. Synlett 1995, 339; Andreu, C.; Marco, J. A.; Asensio, G. J. Chem. Soc., Perkin Trans. I 1990, 3209.
38. 8. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246; Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536; Sha, C.-K.; Shen, C-Y.; Lee, R.-S.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283; Zylber, J.; Tubul, A.; Brun, P. Tetrahedron: Asymmetry 1995, 6, 337. 9. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771; Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509; Takahashi, T.; Namiki, T.; Takeuchi, Y.; Koizumi, T. Chem. Pharm. Bull. 1988, 36, 3213; Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1990, 3065; Takahashi, T.; Kotsubo, H.; Koizumi, T. Ibid. 1991, 1667; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730; Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
39. 8. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246; Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536; Sha, C.-K.; Shen, C-Y.; Lee, R.-S.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283; Zylber, J.; Tubul, A.; Brun, P. Tetrahedron: Asymmetry 1995, 6, 337. 9. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771; Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509; Takahashi, T.; Namiki, T.; Takeuchi, Y.; Koizumi, T. Chem. Pharm. Bull. 1988, 36, 3213; Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1990, 3065; Takahashi, T.; Kotsubo, H.; Koizumi, T. Ibid. 1991, 1667; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730; Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
40. 8. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246; Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536; Sha, C.-K.; Shen, C-Y.; Lee, R.-S.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283; Zylber, J.; Tubul, A.; Brun, P. Tetrahedron: Asymmetry 1995, 6, 337. 9. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771; Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509; Takahashi, T.; Namiki, T.; Takeuchi, Y.; Koizumi, T. Chem. Pharm. Bull. 1988, 36, 3213; Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1990, 3065; Takahashi, T.; Kotsubo, H.; Koizumi, T. Ibid. 1991, 1667; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730; Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
41. 8. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246; Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536; Sha, C.-K.; Shen, C-Y.; Lee, R.-S.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283; Zylber, J.; Tubul, A.; Brun, P. Tetrahedron: Asymmetry 1995, 6, 337. 9. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771; Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509; Takahashi, T.; Namiki, T.; Takeuchi, Y.; Koizumi, T. Chem. Pharm. Bull. 1988, 36, 3213; Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1990, 3065; Takahashi, T.; Kotsubo, H.; Koizumi, T. Ibid. 1991, 1667; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730; Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
42. 8. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246; Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536; Sha, C.-K.; Shen, C-Y.; Lee, R.-S.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283; Zylber, J.; Tubul, A.; Brun, P. Tetrahedron: Asymmetry 1995, 6, 337. 9. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771; Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509; Takahashi, T.; Namiki, T.; Takeuchi, Y.; Koizumi, T. Chem. Pharm. Bull. 1988, 36, 3213; Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1990, 3065; Takahashi, T.; Kotsubo, H.; Koizumi, T. Ibid. 1991, 1667; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730; Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
43. 8. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246; Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536; Sha, C.-K.; Shen, C-Y.; Lee, R.-S.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283; Zylber, J.; Tubul, A.; Brun, P. Tetrahedron: Asymmetry 1995, 6, 337. 9. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771; Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509; Takahashi, T.; Namiki, T.; Takeuchi, Y.; Koizumi, T. Chem. Pharm. Bull. 1988, 36, 3213; Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1990, 3065; Takahashi, T.; Kotsubo, H.; Koizumi, T. Ibid. 1991, 1667; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730; Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
44. 8. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246; Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536; Sha, C.-K.; Shen, C-Y.; Lee, R.-S.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283; Zylber, J.; Tubul, A.; Brun, P. Tetrahedron: Asymmetry 1995, 6, 337. 9. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771; Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509; Takahashi, T.; Namiki, T.; Takeuchi, Y.; Koizumi, T. Chem. Pharm. Bull. 1988, 36, 3213; Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1990, 3065; Takahashi, T.; Kotsubo, H.; Koizumi, T. Ibid. 1991, 1667; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730; Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
45. 8. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246; Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536; Sha, C.-K.; Shen, C-Y.; Lee, R.-S.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283; Zylber, J.; Tubul, A.; Brun, P. Tetrahedron: Asymmetry 1995, 6, 337. 9. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771; Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509; Takahashi, T.; Namiki, T.; Takeuchi, Y.; Koizumi, T. Chem. Pharm. Bull. 1988, 36, 3213; Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1990, 3065; Takahashi, T.; Kotsubo, H.; Koizumi, T. Ibid. 1991, 1667; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730; Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
46. 8. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246; Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536; Sha, C.-K.; Shen, C-Y.; Lee, R.-S.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283; Zylber, J.; Tubul, A.; Brun, P. Tetrahedron: Asymmetry 1995, 6, 337. 9. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771; Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509; Takahashi, T.; Namiki, T.; Takeuchi, Y.; Koizumi, T. Chem. Pharm. Bull. 1988, 36, 3213; Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1990, 3065; Takahashi, T.; Kotsubo, H.; Koizumi, T. Ibid. 1991, 1667; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730; Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
47. 8. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246; Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536; Sha, C.-K.; Shen, C-Y.; Lee, R.-S.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283; Zylber, J.; Tubul, A.; Brun, P. Tetrahedron: Asymmetry 1995, 6, 337. 9. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771; Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509; Takahashi, T.; Namiki, T.; Takeuchi, Y.; Koizumi, T. Chem. Pharm. Bull. 1988, 36, 3213; Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1990, 3065; Takahashi, T.; Kotsubo, H.; Koizumi, T. Ibid. 1991, 1667; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730; Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
48. 8. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246; Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536; Sha, C.-K.; Shen, C-Y.; Lee, R.-S.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283; Zylber, J.; Tubul, A.; Brun, P. Tetrahedron: Asymmetry 1995, 6, 337. 9. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771; Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509; Takahashi, T.; Namiki, T.; Takeuchi, Y.; Koizumi, T. Chem. Pharm. Bull. 1988, 36, 3213; Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1990, 3065; Takahashi, T.; Kotsubo, H.; Koizumi, T. Ibid. 1991, 1667; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730; Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
49. 8. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246; Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536; Sha, C.-K.; Shen, C-Y.; Lee, R.-S.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283; Zylber, J.; Tubul, A.; Brun, P. Tetrahedron: Asymmetry 1995, 6, 337. 9. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771; Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509; Takahashi, T.; Namiki, T.; Takeuchi, Y.; Koizumi, T. Chem. Pharm. Bull. 1988, 36, 3213; Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1990, 3065; Takahashi, T.; Kotsubo, H.; Koizumi, T. Ibid. 1991, 1667; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730; Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
50. 8. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246; Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536; Sha, C.-K.; Shen, C-Y.; Lee, R.-S.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283; Zylber, J.; Tubul, A.; Brun, P. Tetrahedron: Asymmetry 1995, 6, 337. 9. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771; Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509; Takahashi, T.; Namiki, T.; Takeuchi, Y.; Koizumi, T. Chem. Pharm. Bull. 1988, 36, 3213; Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1990, 3065; Takahashi, T.; Kotsubo, H.; Koizumi, T. Ibid. 1991, 1667; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730; Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
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58. 14. Kihara, N.; Morimoto, T.; Nakanishi, T. Jpn. Kokai Tokkyo Koho JP 6137, 796[86 37, 796]; Chem. Abstr. 1986, 105, 153338c; see also the protein phosphatase 2A inhibition by cantharidin analogues: McCluskey, A.; Taylor, C.; Quinn, R. J.; Suganuma, M.; Fujiki, H. Bioorg. Med. Chem. Lett. 1996, 6, 1025.
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60. 15. Quarroz, D.; Sonney, J.-M.; Chollet, A.; Florey, A.; Vogel, P. Org. Magn. Reson. 1977, 9, 611; Vogel, P.; in "Advances in Theoretically Interesting Molecules", Thummel, R. P.; Ed., JAI Press Inc., Greenwich, CT, USA, 1989, Vol. I., p. 201-355.
61. 16. Charney, E. "The Molecular Basis of Optical Activity", Wiley, New York, 1979, pp. 217-226; Burgstahler, A. W.; Barkhurst, R. C.; Gawronski, J. K., in "Modern Methods of Steroid Analysis", Heftmann, Ed., Academic Press, New York, 1973, Chap. 16, pp. 349-379; Snatzke, G.; Snatzke, F. in "Fundamental Aspects and Recent Development in Optical Rotatory Dispersion and Circular Dichroism", Ciardelli, F.; Salvadori, P., Eds. Heyden & Son, New York, 1973, Chap. 3, 5; Snatzke, G. in "Optical Activity and Chiral Discrimination", Mason, S. F., Ed., Reidel, D. Dordrecht, 1979, pp. 48-55; Weiss, U.; Ziffer, H.; Charney, E. Tetrahedron 1965, 21, 3105; Charney, E.; Ziffer, H.; Weiss, U. Tetrahedron 1965, 21, 3121; Burgstahler, A. W.; Ziffer, H.; Weiss, U. J. Am. Chem. Soc. 1961, 83, 4660; Moscowitz, A.; Charney, E.; Weiss, U.; Ziffer, H. Ibid. 1961, 83, 4661; Charney, E. Tetrahedron 1965, 21, 3127; Lightner, D. A.; Bouman, T. D.; Gawronski, J. K.; Gawronska, K.; Chappuis, J. L.; Crist, B. V.; Hansen, A. E. J. Am. Chem. Soc. 1981, 103, 5314; Burgstahler, A. W.; Wahl, G.; Dang, N.; Sanders, M. E.; Nemirovsky, A. Ibid. 1982, 104, 6873.
62. 16. Charney, E. "The Molecular Basis of Optical Activity", Wiley, New York, 1979, pp. 217-226; Burgstahler, A. W.; Barkhurst, R. C.; Gawronski, J. K., in "Modern Methods of Steroid Analysis", Heftmann, Ed., Academic Press, New York, 1973, Chap. 16, pp. 349-379; Snatzke, G.; Snatzke, F. in "Fundamental Aspects and Recent Development in Optical Rotatory Dispersion and Circular Dichroism", Ciardelli, F.; Salvadori, P., Eds. Heyden & Son, New York, 1973, Chap. 3, 5; Snatzke, G. in "Optical Activity and Chiral Discrimination", Mason, S. F., Ed., Reidel, D. Dordrecht, 1979, pp. 48-55; Weiss, U.; Ziffer, H.; Charney, E. Tetrahedron 1965, 21, 3105; Charney, E.; Ziffer, H.; Weiss, U. Tetrahedron 1965, 21, 3121; Burgstahler, A. W.; Ziffer, H.; Weiss, U. J. Am. Chem. Soc. 1961, 83, 4660; Moscowitz, A.; Charney, E.; Weiss, U.; Ziffer, H. Ibid. 1961, 83, 4661; Charney, E. Tetrahedron 1965, 21, 3127; Lightner, D. A.; Bouman, T. D.; Gawronski, J. K.; Gawronska, K.; Chappuis, J. L.; Crist, B. V.; Hansen, A. E. J. Am. Chem. Soc. 1981, 103, 5314; Burgstahler, A. W.; Wahl, G.; Dang, N.; Sanders, M. E.; Nemirovsky, A. Ibid. 1982, 104, 6873.
63. 16. Charney, E. "The Molecular Basis of Optical Activity", Wiley, New York, 1979, pp. 217-226; Burgstahler, A. W.; Barkhurst, R. C.; Gawronski, J. K., in "Modern Methods of Steroid Analysis", Heftmann, Ed., Academic Press, New York, 1973, Chap. 16, pp. 349-379; Snatzke, G.; Snatzke, F. in "Fundamental Aspects and Recent Development in Optical Rotatory Dispersion and Circular Dichroism", Ciardelli, F.; Salvadori, P., Eds. Heyden & Son, New York, 1973, Chap. 3, 5; Snatzke, G. in "Optical Activity and Chiral Discrimination", Mason, S. F., Ed., Reidel, D. Dordrecht, 1979, pp. 48-55; Weiss, U.; Ziffer, H.; Charney, E. Tetrahedron 1965, 21, 3105; Charney, E.; Ziffer, H.; Weiss, U. Tetrahedron 1965, 21, 3121; Burgstahler, A. W.; Ziffer, H.; Weiss, U. J. Am. Chem. Soc. 1961, 83, 4660; Moscowitz, A.; Charney, E.; Weiss, U.; Ziffer, H. Ibid. 1961, 83, 4661; Charney, E. Tetrahedron 1965, 21, 3127; Lightner, D. A.; Bouman, T. D.; Gawronski, J. K.; Gawronska, K.; Chappuis, J. L.; Crist, B. V.; Hansen, A. E. J. Am. Chem. Soc. 1981, 103, 5314; Burgstahler, A. W.; Wahl, G.; Dang, N.; Sanders, M. E.; Nemirovsky, A. Ibid. 1982, 104, 6873.
64. 16. Charney, E. "The Molecular Basis of Optical Activity", Wiley, New York, 1979, pp. 217-226; Burgstahler, A. W.; Barkhurst, R. C.; Gawronski, J. K., in "Modern Methods of Steroid Analysis", Heftmann, Ed., Academic Press, New York, 1973, Chap. 16, pp. 349-379; Snatzke, G.; Snatzke, F. in "Fundamental Aspects and Recent Development in Optical Rotatory Dispersion and Circular Dichroism", Ciardelli, F.; Salvadori, P., Eds. Heyden & Son, New York, 1973, Chap. 3, 5; Snatzke, G. in "Optical Activity and Chiral Discrimination", Mason, S. F., Ed., Reidel, D. Dordrecht, 1979, pp. 48-55; Weiss, U.; Ziffer, H.; Charney, E. Tetrahedron 1965, 21, 3105; Charney, E.; Ziffer, H.; Weiss, U. Tetrahedron 1965, 21, 3121; Burgstahler, A. W.; Ziffer, H.; Weiss, U. J. Am. Chem. Soc. 1961, 83, 4660; Moscowitz, A.; Charney, E.; Weiss, U.; Ziffer, H. Ibid. 1961, 83, 4661; Charney, E. Tetrahedron 1965, 21, 3127; Lightner, D. A.; Bouman, T. D.; Gawronski, J. K.; Gawronska, K.; Chappuis, J. L.; Crist, B. V.; Hansen, A. E. J. Am. Chem. Soc. 1981, 103, 5314; Burgstahler, A. W.; Wahl, G.; Dang, N.; Sanders, M. E.; Nemirovsky, A. Ibid. 1982, 104, 6873.
65. 16. Charney, E. "The Molecular Basis of Optical Activity", Wiley, New York, 1979, pp. 217-226; Burgstahler, A. W.; Barkhurst, R. C.; Gawronski, J. K., in "Modern Methods of Steroid Analysis", Heftmann, Ed., Academic Press, New York, 1973, Chap. 16, pp. 349-379; Snatzke, G.; Snatzke, F. in "Fundamental Aspects and Recent Development in Optical Rotatory Dispersion and Circular Dichroism", Ciardelli, F.; Salvadori, P., Eds. Heyden & Son, New York, 1973, Chap. 3, 5; Snatzke, G. in "Optical Activity and Chiral Discrimination", Mason, S. F., Ed., Reidel, D. Dordrecht, 1979, pp. 48-55; Weiss, U.; Ziffer, H.; Charney, E. Tetrahedron 1965, 21, 3105; Charney, E.; Ziffer, H.; Weiss, U. Tetrahedron 1965, 21, 3121; Burgstahler, A. W.; Ziffer, H.; Weiss, U. J. Am. Chem. Soc. 1961, 83, 4660; Moscowitz, A.; Charney, E.; Weiss, U.; Ziffer, H. Ibid. 1961, 83, 4661; Charney, E. Tetrahedron 1965, 21, 3127; Lightner, D. A.; Bouman, T. D.; Gawronski, J. K.; Gawronska, K.; Chappuis, J. L.; Crist, B. V.; Hansen, A. E. J. Am. Chem. Soc. 1981, 103, 5314; Burgstahler, A. W.; Wahl, G.; Dang, N.; Sanders, M. E.; Nemirovsky, A. Ibid. 1982, 104, 6873.
66. 16. Charney, E. "The Molecular Basis of Optical Activity", Wiley, New York, 1979, pp. 217-226; Burgstahler, A. W.; Barkhurst, R. C.; Gawronski, J. K., in "Modern Methods of Steroid Analysis", Heftmann, Ed., Academic Press, New York, 1973, Chap. 16, pp. 349-379; Snatzke, G.; Snatzke, F. in "Fundamental Aspects and Recent Development in Optical Rotatory Dispersion and Circular Dichroism", Ciardelli, F.; Salvadori, P., Eds. Heyden & Son, New York, 1973, Chap. 3, 5; Snatzke, G. in "Optical Activity and Chiral Discrimination", Mason, S. F., Ed., Reidel, D. Dordrecht, 1979, pp. 48-55; Weiss, U.; Ziffer, H.; Charney, E. Tetrahedron 1965, 21, 3105; Charney, E.; Ziffer, H.; Weiss, U. Tetrahedron 1965, 21, 3121; Burgstahler, A. W.; Ziffer, H.; Weiss, U. J. Am. Chem. Soc. 1961, 83, 4660; Moscowitz, A.; Charney, E.; Weiss, U.; Ziffer, H. Ibid. 1961, 83, 4661; Charney, E. Tetrahedron 1965, 21, 3127; Lightner, D. A.; Bouman, T. D.; Gawronski, J. K.; Gawronska, K.; Chappuis, J. L.; Crist, B. V.; Hansen, A. E. J. Am. Chem. Soc. 1981, 103, 5314; Burgstahler, A. W.; Wahl, G.; Dang, N.; Sanders, M. E.; Nemirovsky, A. Ibid. 1982, 104, 6873.
67. 16. Charney, E. "The Molecular Basis of Optical Activity", Wiley, New York, 1979, pp. 217-226; Burgstahler, A. W.; Barkhurst, R. C.; Gawronski, J. K., in "Modern Methods of Steroid Analysis", Heftmann, Ed., Academic Press, New York, 1973, Chap. 16, pp. 349-379; Snatzke, G.; Snatzke, F. in "Fundamental Aspects and Recent Development in Optical Rotatory Dispersion and Circular Dichroism", Ciardelli, F.; Salvadori, P., Eds. Heyden & Son, New York, 1973, Chap. 3, 5; Snatzke, G. in "Optical Activity and Chiral Discrimination", Mason, S. F., Ed., Reidel, D. Dordrecht, 1979, pp. 48-55; Weiss, U.; Ziffer, H.; Charney, E. Tetrahedron 1965, 21, 3105; Charney, E.; Ziffer, H.; Weiss, U. Tetrahedron 1965, 21, 3121; Burgstahler, A. W.; Ziffer, H.; Weiss, U. J. Am. Chem. Soc. 1961, 83, 4660; Moscowitz, A.; Charney, E.; Weiss, U.; Ziffer, H. Ibid. 1961, 83, 4661; Charney, E. Tetrahedron 1965, 21, 3127; Lightner, D. A.; Bouman, T. D.; Gawronski, J. K.; Gawronska, K.; Chappuis, J. L.; Crist, B. V.; Hansen, A. E. J. Am. Chem. Soc. 1981, 103, 5314; Burgstahler, A. W.; Wahl, G.; Dang, N.; Sanders, M. E.; Nemirovsky, A. Ibid. 1982, 104, 6873.
68. 16. Charney, E. "The Molecular Basis of Optical Activity", Wiley, New York, 1979, pp. 217-226; Burgstahler, A. W.; Barkhurst, R. C.; Gawronski, J. K., in "Modern Methods of Steroid Analysis", Heftmann, Ed., Academic Press, New York, 1973, Chap. 16, pp. 349-379; Snatzke, G.; Snatzke, F. in "Fundamental Aspects and Recent Development in Optical Rotatory Dispersion and Circular Dichroism", Ciardelli, F.; Salvadori, P., Eds. Heyden & Son, New York, 1973, Chap. 3, 5; Snatzke, G. in "Optical Activity and Chiral Discrimination", Mason, S. F., Ed., Reidel, D. Dordrecht, 1979, pp. 48-55; Weiss, U.; Ziffer, H.; Charney, E. Tetrahedron 1965, 21, 3105; Charney, E.; Ziffer, H.; Weiss, U. Tetrahedron 1965, 21, 3121; Burgstahler, A. W.; Ziffer, H.; Weiss, U. J. Am. Chem. Soc. 1961, 83, 4660; Moscowitz, A.; Charney, E.; Weiss, U.; Ziffer, H. Ibid. 1961, 83, 4661; Charney, E. Tetrahedron 1965, 21, 3127; Lightner, D. A.; Bouman, T. D.; Gawronski, J. K.; Gawronska, K.; Chappuis, J. L.; Crist, B. V.; Hansen, A. E. J. Am. Chem. Soc. 1981, 103, 5314; Burgstahler, A. W.; Wahl, G.; Dang, N.; Sanders, M. E.; Nemirovsky, A. Ibid. 1982, 104, 6873.
69. 16. Charney, E. "The Molecular Basis of Optical Activity", Wiley, New York, 1979, pp. 217-226; Burgstahler, A. W.; Barkhurst, R. C.; Gawronski, J. K., in "Modern Methods of Steroid Analysis", Heftmann, Ed., Academic Press, New York, 1973, Chap. 16, pp. 349-379; Snatzke, G.; Snatzke, F. in "Fundamental Aspects and Recent Development in Optical Rotatory Dispersion and Circular Dichroism", Ciardelli, F.; Salvadori, P., Eds. Heyden & Son, New York, 1973, Chap. 3, 5; Snatzke, G. in "Optical Activity and Chiral Discrimination", Mason, S. F., Ed., Reidel, D. Dordrecht, 1979, pp. 48-55; Weiss, U.; Ziffer, H.; Charney, E. Tetrahedron 1965, 21, 3105; Charney, E.; Ziffer, H.; Weiss, U. Tetrahedron 1965, 21, 3121; Burgstahler, A. W.; Ziffer, H.; Weiss, U. J. Am. Chem. Soc. 1961, 83, 4660; Moscowitz, A.; Charney, E.; Weiss, U.; Ziffer, H. Ibid. 1961, 83, 4661; Charney, E. Tetrahedron 1965, 21, 3127; Lightner, D. A.; Bouman, T. D.; Gawronski, J. K.; Gawronska, K.; Chappuis, J. L.; Crist, B. V.; Hansen, A. E. J. Am. Chem. Soc. 1981, 103, 5314; Burgstahler, A. W.; Wahl, G.; Dang, N.; Sanders, M. E.; Nemirovsky, A. Ibid. 1982, 104, 6873.
70. 16. Charney, E. "The Molecular Basis of Optical Activity", Wiley, New York, 1979, pp. 217-226; Burgstahler, A. W.; Barkhurst, R. C.; Gawronski, J. K., in "Modern Methods of Steroid Analysis", Heftmann, Ed., Academic Press, New York, 1973, Chap. 16, pp. 349-379; Snatzke, G.; Snatzke, F. in "Fundamental Aspects and Recent Development in Optical Rotatory Dispersion and Circular Dichroism", Ciardelli, F.; Salvadori, P., Eds. Heyden & Son, New York, 1973, Chap. 3, 5; Snatzke, G. in "Optical Activity and Chiral Discrimination", Mason, S. F., Ed., Reidel, D. Dordrecht, 1979, pp. 48-55; Weiss, U.; Ziffer, H.; Charney, E. Tetrahedron 1965, 21, 3105; Charney, E.; Ziffer, H.; Weiss, U. Tetrahedron 1965, 21, 3121; Burgstahler, A. W.; Ziffer, H.; Weiss, U. J. Am. Chem. Soc. 1961, 83, 4660; Moscowitz, A.; Charney, E.; Weiss, U.; Ziffer, H. Ibid. 1961, 83, 4661; Charney, E. Tetrahedron 1965, 21, 3127; Lightner, D. A.; Bouman, T. D.; Gawronski, J. K.; Gawronska, K.; Chappuis, J. L.; Crist, B. V.; Hansen, A. E. J. Am. Chem. Soc. 1981, 103, 5314; Burgstahler, A. W.; Wahl, G.; Dang, N.; Sanders, M. E.; Nemirovsky, A. Ibid. 1982, 104, 6873.
71. 16. Charney, E. "The Molecular Basis of Optical Activity", Wiley, New York, 1979, pp. 217-226; Burgstahler, A. W.; Barkhurst, R. C.; Gawronski, J. K., in "Modern Methods of Steroid Analysis", Heftmann, Ed., Academic Press, New York, 1973, Chap. 16, pp. 349-379; Snatzke, G.; Snatzke, F. in "Fundamental Aspects and Recent Development in Optical Rotatory Dispersion and Circular Dichroism", Ciardelli, F.; Salvadori, P., Eds. Heyden & Son, New York, 1973, Chap. 3, 5; Snatzke, G. in "Optical Activity and Chiral Discrimination", Mason, S. F., Ed., Reidel, D. Dordrecht, 1979, pp. 48-55; Weiss, U.; Ziffer, H.; Charney, E. Tetrahedron 1965, 21, 3105; Charney, E.; Ziffer, H.; Weiss, U. Tetrahedron 1965, 21, 3121; Burgstahler, A. W.; Ziffer, H.; Weiss, U. J. Am. Chem. Soc. 1961, 83, 4660; Moscowitz, A.; Charney, E.; Weiss, U.; Ziffer, H. Ibid. 1961, 83, 4661; Charney, E. Tetrahedron 1965, 21, 3127; Lightner, D. A.; Bouman, T. D.; Gawronski, J. K.; Gawronska, K.; Chappuis, J. L.; Crist, B. V.; Hansen, A. E. J. Am. Chem. Soc. 1981, 103, 5314; Burgstahler, A. W.; Wahl, G.; Dang, N.; Sanders, M. E.; Nemirovsky, A. Ibid. 1982, 104, 6873.
72. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
73. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
74. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
75. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
76. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
77. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
78. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
79. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
80. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
81. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
82. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
83. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
84. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
85. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
86. 17. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C-H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1978, 53, 160; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; Idem, Ibid. 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Weigang, O. E. J. Am. Chem. Soc. 1979, 101, 1965; Moriarty, R. M.; Paaren, H. E.; Weiss, U.; Whalley, W. B. Ibid. 1979, 101, 6804; Duraisamy, M.; Walborsky, H. M. Ibid. 1983, 105, 3264; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1034.
87. 18. Johnson, C. K. ORTEP, Report ORNL-5138, 1976, Oak Ridge National Laboratory, Tennessee, USA.
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89. 19. Métral, J.-L.; Lauterwein, J.; Vogel, P. Helv. Chim. Acta 1986, 69, 1287; Antonsson, T.; Vogel, P. Tetrahedron Lett. 1990, 31, 89.
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92. 22. Main, P.; Fiske, S. J.; Hull, S. E.; Lessinger, L.; Germain, G.; DeClerq, J. P.; Woolfson, M. M., MULTAN 80, University of York, England, 1980.
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94. 24. Fair, C. K., MolEN, An Interactive Intelligent System for Crystal Structure Analysis, User Manual, Enraf-Nonius, Delft, The Netherlands, 1990.
95. 25. Crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC-101 . Copies of the data can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge, CB2 IE7, UK (Fax: +44 (0) 1223 33 60 33; E-mail: teched@chemcrys.cam.ac.uk).