Synthesis of tricyclopolyprenols via a radical addition and a stereoselective elimination. Part I: Methodology

Tetrahedron

Volumn 54, Issue 1-2, 1998, Pages 97-106

  Jenn, Thierry ^a   Heissler, Denis ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

TERPENE DERIVATIVE; TRICYCLOPOLYPRENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031986059     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10259-9     Document Type: Article

References (51)

1. 1. Aquino-Neto, F. R.; Restle, A.; Connan, J.; Albrecht, P.; Ourisson, G. Tetrahedron Lett. 1982, 23, 2027-2030. Ekweozor, C. M.; Strausz, O. P. Ibid. 1982, 23, 2711-2714. Moldowan, J. M.; Seifert, W. K.; Gallegos, E. J. Geochim. Cosmochim. Acta 1983, 47, 1531-1534. Heissler, D.; Ocampo, R.; Albrecht, P.; Riehl, J. J.; Ourisson, G. J. Chem. Soc., Chem. Commun. 1984, 496-498. González Sierra, M.; Cravero, R. M.; Laborde, M. A.; Rúveda, E. A. Ibid. 1984, 417-418; J. Chem. Soc., Perkin Trans. 1, 1985, 1227-1231.
2. 1. Aquino-Neto, F. R.; Restle, A.; Connan, J.; Albrecht, P.; Ourisson, G. Tetrahedron Lett. 1982, 23, 2027-2030. Ekweozor, C. M.; Strausz, O. P. Ibid. 1982, 23, 2711-2714. Moldowan, J. M.; Seifert, W. K.; Gallegos, E. J. Geochim. Cosmochim. Acta 1983, 47, 1531-1534. Heissler, D.; Ocampo, R.; Albrecht, P.; Riehl, J. J.; Ourisson, G. J. Chem. Soc., Chem. Commun. 1984, 496-498. González Sierra, M.; Cravero, R. M.; Laborde, M. A.; Rúveda, E. A. Ibid. 1984, 417-418; J. Chem. Soc., Perkin Trans. 1, 1985, 1227-1231.
3. 1. Aquino-Neto, F. R.; Restle, A.; Connan, J.; Albrecht, P.; Ourisson, G. Tetrahedron Lett. 1982, 23, 2027-2030. Ekweozor, C. M.; Strausz, O. P. Ibid. 1982, 23, 2711-2714. Moldowan, J. M.; Seifert, W. K.; Gallegos, E. J. Geochim. Cosmochim. Acta 1983, 47, 1531-1534. Heissler, D.; Ocampo, R.; Albrecht, P.; Riehl, J. J.; Ourisson, G. J. Chem. Soc., Chem. Commun. 1984, 496-498. González Sierra, M.; Cravero, R. M.; Laborde, M. A.; Rúveda, E. A. Ibid. 1984, 417-418; J. Chem. Soc., Perkin Trans. 1, 1985, 1227-1231.
4. 1. Aquino-Neto, F. R.; Restle, A.; Connan, J.; Albrecht, P.; Ourisson, G. Tetrahedron Lett. 1982, 23, 2027-2030. Ekweozor, C. M.; Strausz, O. P. Ibid. 1982, 23, 2711-2714. Moldowan, J. M.; Seifert, W. K.; Gallegos, E. J. Geochim. Cosmochim. Acta 1983, 47, 1531-1534. Heissler, D.; Ocampo, R.; Albrecht, P.; Riehl, J. J.; Ourisson, G. J. Chem. Soc., Chem. Commun. 1984, 496-498. González Sierra, M.; Cravero, R. M.; Laborde, M. A.; Rúveda, E. A. Ibid. 1984, 417-418; J. Chem. Soc., Perkin Trans. 1, 1985, 1227-1231.
5. 1. Aquino-Neto, F. R.; Restle, A.; Connan, J.; Albrecht, P.; Ourisson, G. Tetrahedron Lett. 1982, 23, 2027-2030. Ekweozor, C. M.; Strausz, O. P. Ibid. 1982, 23, 2711-2714. Moldowan, J. M.; Seifert, W. K.; Gallegos, E. J. Geochim. Cosmochim. Acta 1983, 47, 1531-1534. Heissler, D.; Ocampo, R.; Albrecht, P.; Riehl, J. J.; Ourisson, G. J. Chem. Soc., Chem. Commun. 1984, 496-498. González Sierra, M.; Cravero, R. M.; Laborde, M. A.; Rúveda, E. A. Ibid. 1984, 417-418; J. Chem. Soc., Perkin Trans. 1, 1985, 1227-1231.
6. 1. Aquino-Neto, F. R.; Restle, A.; Connan, J.; Albrecht, P.; Ourisson, G. Tetrahedron Lett. 1982, 23, 2027-2030. Ekweozor, C. M.; Strausz, O. P. Ibid. 1982, 23, 2711-2714. Moldowan, J. M.; Seifert, W. K.; Gallegos, E. J. Geochim. Cosmochim. Acta 1983, 47, 1531-1534. Heissler, D.; Ocampo, R.; Albrecht, P.; Riehl, J. J.; Ourisson, G. J. Chem. Soc., Chem. Commun. 1984, 496-498. González Sierra, M.; Cravero, R. M.; Laborde, M. A.; Rúveda, E. A. Ibid. 1984, 417-418; J. Chem. Soc., Perkin Trans. 1, 1985, 1227-1231.
7. 2. Krajewski-Bertrand, M. A.; Hayer, M.; Wolff, G.; Milon, A.; Albrecht, A. M.; Heissler, D.; Nakatani, Y; Ourisson, G. Tetrahedron 1990, 46, 3143-3154; Krajewski-Bertrand, M.-A.; Milon, A.; Nakatani, Y.; Ourisson, G. Biochim. Biophys. Acta 1992, 1105, 213-220.
8. 2. Krajewski-Bertrand, M. A.; Hayer, M.; Wolff, G.; Milon, A.; Albrecht, A. M.; Heissler, D.; Nakatani, Y; Ourisson, G. Tetrahedron 1990, 46, 3143-3154; Krajewski-Bertrand, M.-A.; Milon, A.; Nakatani, Y.; Ourisson, G. Biochim. Biophys. Acta 1992, 1105, 213-220.
9. 3. Ourisson, G.; Albrecht, P.; Rohmer, M. Trends Biochem. Sci. 1982, 7, 236-239. Ourisson, G.; Albrecht, P. Acc. Chem. Res. 1992, 25, 398-402. Ourisson, G.; Nakatani, Y. Chemistry & Biology 1994, 1, 11-23.
10. 3. Ourisson, G.; Albrecht, P.; Rohmer, M. Trends Biochem. Sci. 1982, 7, 236-239. Ourisson, G.; Albrecht, P. Acc. Chem. Res. 1992, 25, 398-402. Ourisson, G.; Nakatani, Y. Chemistry & Biology 1994, 1, 11-23.
11. 3. Ourisson, G.; Albrecht, P.; Rohmer, M. Trends Biochem. Sci. 1982, 7, 236-239. Ourisson, G.; Albrecht, P. Acc. Chem. Res. 1992, 25, 398-402. Ourisson, G.; Nakatani, Y. Chemistry & Biology 1994, 1, 11-23.
12. 4. See following paper. Preliminary communications: a) Heissler, D.; Jenn, T.; Nagano, H. Tetrahedron Lett. 1991, 32, 7587-7590.
13. b) Jenn, T.; Heissler, D. Ibid. 1992, 33, 7227-7228.
14. 5. Corey, E. J.; Burk, R. M. Tetrahedron Lett. 1987, 28, 6413-6416.
15. 6. Heissler, D.; Ladenburger, C. Tetrahedron 1988, 44, 2513-2521.
16. 7. Ladenburger, C; Heissler, D. J. Chem. Research (S) 1991, 330.
17. 8 Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986, pp. 36-140. Curran, D. P. Synthesis 1988, 417-439;
18. 8 Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986, pp. 36-140. Curran, D. P. Synthesis 1988, 417-439;
19. Radical addition reactions. In Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press: Oxford, vol. 4, 1991; pp. 715-777.
20. 9. We dreaded that the homoallylic radical A could rearrange into the radical C before adding to the activated double bond. However, the results obtained by others with the radical deriving from 3-(bromomethyl)-cyclohex-1-ene led us to be reasonably optimistic: Friederich, E. C.; Holmstead, R. L. J. Org. Chem. 1972, 37, 2550-2554. (formula presented)
21. 10. Haynes, R. K.; Holden, M. Aust. J. Chem. 1982, 35, 517-524. Wiley, G. A.; Hershkowitz, R.L.; Rein, B. M.; Chung, B. C. J. Am. Chem. Soc. 1964, 86, 964-965.
22. 10. Haynes, R. K.; Holden, M. Aust. J. Chem. 1982, 35, 517-524. Wiley, G. A.; Hershkowitz, R.L.; Rein, B. M.; Chung, B. C. J. Am. Chem. Soc. 1964, 86, 964-965.
23. 11. Keck, G. E.; Yates, J. B. J. Am. Chem. Soc. 1982, 104, 5829-5831. Kosugi, M.; Kurino, K.; Takayama, K.; Migita, T. J. Organometal. Chem. 1973, 56, C11-C13. Grignon, J.; Pereyre, M. Ibid. 1973, 61, C33-C35.
24. 11. Keck, G. E.; Yates, J. B. J. Am. Chem. Soc. 1982, 104, 5829-5831. Kosugi, M.; Kurino, K.; Takayama, K.; Migita, T. J. Organometal. Chem. 1973, 56, C11-C13. Grignon, J.; Pereyre, M. Ibid. 1973, 61, C33-C35.
25. 11. Keck, G. E.; Yates, J. B. J. Am. Chem. Soc. 1982, 104, 5829-5831. Kosugi, M.; Kurino, K.; Takayama, K.; Migita, T. J. Organometal. Chem. 1973, 56, C11-C13. Grignon, J.; Pereyre, M. Ibid. 1973, 61, C33-C35.
26. 12. Keck, G. E.; Tafesh, A. M. J. Org. Chem. 1989, 54, 5845-5846. Keck, G. E.; Byers, J. H. Ibid. 1985, 50, 5442-5444.
27. 12. Keck, G. E.; Tafesh, A. M. J. Org. Chem. 1989, 54, 5845-5846. Keck, G. E.; Byers, J. H. Ibid. 1985, 50, 5442-5444.
28. 13. a) Baylis, A. B.; Hillman, M. E. D. German Patent 1972, 2155113; Chem. Abstr. 1972, 77, 34174q.
29. 13. a) Baylis, A. B.; Hillman, M. E. D. German Patent 1972, 2155113; Chem. Abstr. 1972, 77, 34174q.
30. b) Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1983, 22, 795-796.
31. c) Amri, H.; Villieras, J. Tetrahedron Lett. 1986, 27, 4307-4308.
32. d) Basavaiah, D.; Gowriswari, V. V. L. Synth. Commun. 1987, 17, 587-591.
33. e) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670.
34. f) Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001-8062.
35. 1H-NMR on the alkenic H-3 triplet which was at δ = 6.09 for the nitrile 12Z and at δ = 6.39 for the nitrile 12E.
36. 15. Ameer, F.; Drewes, S. E.; Freese, S.; Kaye, P. T. Synth. Commun. 1988, 18, 495-500.
37. 1H-NMR on the alkenic H-3 triplet which was at δ = 6.81 for the ester 15E and at δ = 5.79 for the ester 15Z.
38. 17. In recent years, several papers have described the obtention of stereodefined trisubstituted alkenes from Baylis-Hillman adducts by nucleophilic substitution reactions; for a review see ref. 13f, pp. 8023-8035. See also: Piettre, S.; Heathcock, C. H. Science 1990, 248, 1532-1534. Heathcock, C. H.; Piettre, S.; Ruggeri, R. B.; Ragan, J. A.; Kath, J. C. J. Org. Chem. 1992, 57, 2554-2566.
39. 17. In recent years, several papers have described the obtention of stereodefined trisubstituted alkenes from Baylis-Hillman adducts by nucleophilic substitution reactions; for a review see ref. 13f, pp. 8023-8035. See also: Piettre, S.; Heathcock, C. H. Science 1990, 248, 1532-1534. Heathcock, C. H.; Piettre, S.; Ruggeri, R. B.; Ragan, J. A.; Kath, J. C. J. Org. Chem. 1992, 57, 2554-2566.
40. 18. Brown, H. C.; Kim, S. C.; Krishnamurthy, S. J. Org. Chem. 1980, 45, 1-12.
41. 19. Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1966, 88, 1464-1472.
42. 20. DeChristopher, P. J.; Adamek, J. P.; Lyon, G. D.; Galante, J. J.; Haffner, H. E.; Boggio, R. J.; Baumgarten, R. J. J. Am Chem. Soc. 1969, 91, 2384-2385. Andersen, N. H.; Uh, H. S. Synth. Commun. 1972, 2, 297-302.
43. 20. DeChristopher, P. J.; Adamek, J. P.; Lyon, G. D.; Galante, J. J.; Haffner, H. E.; Boggio, R. J.; Baumgarten, R. J. J. Am Chem. Soc. 1969, 91, 2384-2385. Andersen, N. H.; Uh, H. S. Synth. Commun. 1972, 2, 297-302.
44. 21. Hutchins, R. O.; Kandasamy, D.; Dux, F.; Maryanoff, C. A.; Rotstein, D.; Goldsmith, B.; Burgoyne, W.; Cistone, F.; Dalessandro, J.; Puglis, J. J. Org. Chem. 1978, 43, 2259-2267.
45. 22. Kapnang, H.; Charles, G.; Sondengam, B. L.; Hentchoya Hémo, J. Tetrahedron Lett. 1977, 3469-3472. Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673-1674. Sondengam, B. M.; Hentchoya Hémo, J.; Charles, G. Tetrahedron Lett. 1973, 261-263.
46. 22. Kapnang, H.; Charles, G.; Sondengam, B. L.; Hentchoya Hémo, J. Tetrahedron Lett. 1977, 3469-3472. Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673-1674. Sondengam, B. M.; Hentchoya Hémo, J.; Charles, G. Tetrahedron Lett. 1973, 261-263.
47. 22. Kapnang, H.; Charles, G.; Sondengam, B. L.; Hentchoya Hémo, J. Tetrahedron Lett. 1977, 3469-3472. Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673-1674. Sondengam, B. M.; Hentchoya Hémo, J.; Charles, G. Tetrahedron Lett. 1973, 261-263.
48. 23. Kometani, T.; Shiotani, S.; Mitsuhashi, K. Chem. Pharm. Bull. 1976, 24, 342-349. Mornet, R.; Gouin, L. Synthesis, 1977, 786-787. Kapnang, H.; Charles, G. Tetrahedron Lett. 1983, 24, 3233-3236. For a review, see: Cooley, J. H.; Evain, E. J. Synthesis 1989, 1-7.
49. 23. Kometani, T.; Shiotani, S.; Mitsuhashi, K. Chem. Pharm. Bull. 1976, 24, 342-349. Mornet, R.; Gouin, L. Synthesis, 1977, 786-787. Kapnang, H.; Charles, G. Tetrahedron Lett. 1983, 24, 3233-3236. For a review, see: Cooley, J. H.; Evain, E. J. Synthesis 1989, 1-7.
50. 23. Kometani, T.; Shiotani, S.; Mitsuhashi, K. Chem. Pharm. Bull. 1976, 24, 342-349. Mornet, R.; Gouin, L. Synthesis, 1977, 786-787. Kapnang, H.; Charles, G. Tetrahedron Lett. 1983, 24, 3233-3236. For a review, see: Cooley, J. H.; Evain, E. J. Synthesis 1989, 1-7.
51. 23. Kometani, T.; Shiotani, S.; Mitsuhashi, K. Chem. Pharm. Bull. 1976, 24, 342-349. Mornet, R.; Gouin, L. Synthesis, 1977, 786-787. Kapnang, H.; Charles, G. Tetrahedron Lett. 1983, 24, 3233-3236. For a review, see: Cooley, J. H.; Evain, E. J. Synthesis 1989, 1-7.