Synthesis of tricyclopolyprenols via a radical addition and a stereoselective elimination, part II: (Z)-tricyclopentaprenol, (E,E)- and (Z,Z)-tricyclohexaprenol, (Z,Z,Z)-tricycloheptaprenol

Tetrahedron

Volumn 54, Issue 1-2, 1998, Pages 107-118

  Jenn, Thierry ^a   Heissler, Denis ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

TERPENE DERIVATIVE; TRICYCLOHEPTAPRENOL; TRICYCLOHEXAPRENOL; TRICYCLOPENTAPRENOL; TRICYCLOPOLYPRENOL DERIVATIVE; UNCLASSIFIED DRUG;

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

EID: 0031986275     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10260-5     Document Type: Article

References (26)

1. 1. Preliminary communications: a) Jenn, T.; Heissler, D. Tetrahedron Lett. 1992, 33, 7227-7228.
2. b) Heissler, D.; Jenn, T.; Nagano, H. Tetrahedron Lett. 1991, 32, 7587-7590.
3. 2. Moldowan, J. M.; Seifert, W. K.; Gallegos, E. J. Geochim. Cosmochim. Acta 1983, 47, 1531-1534.
4. 3. a) Kamaya, R.; Ageta, H. Chem. Pharm. Bull. 1990, 38, 342-346.
5. b) Jenn, T.; Heissler, D. Synlett 1995, 607-608.
6. 4. Baylis, A. B.; Hillman, M. E. D. German Patent 1972, 2155113; Chem. Abstr. 1972, 77, 34174q; Reviews: Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670; Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001-8062.
7. 4. Baylis, A. B.; Hillman, M. E. D. German Patent 1972, 2155113; Chem. Abstr. 1972, 77, 34174q; Reviews: Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670; Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001-8062.
8. 4. Baylis, A. B.; Hillman, M. E. D. German Patent 1972, 2155113; Chem. Abstr. 1972, 77, 34174q; Reviews: Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670; Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001-8062.
9. 4. Baylis, A. B.; Hillman, M. E. D. German Patent 1972, 2155113; Chem. Abstr. 1972, 77, 34174q; Reviews: Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670; Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001-8062.
10. 5. Van Tamelen, E. E.; Curphey, T. J. Tetrahedron Lett. 1962, 121-124. Van Tamelen, E. E.; Storni, A.; Hessler, E. J.; Schwartz, M. A. Bioorg. Chem. 1982, 11, 133-170. A recent paper describes the same transformation in two steps, but with a lower overall yield: Davisson, V. J.; Neal, T. R.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1235-1245.
11. 5. Van Tamelen, E. E.; Curphey, T. J. Tetrahedron Lett. 1962, 121-124. Van Tamelen, E. E.; Storni, A.; Hessler, E. J.; Schwartz, M. A. Bioorg. Chem. 1982, 11, 133-170. A recent paper describes the same transformation in two steps, but with a lower overall yield: Davisson, V. J.; Neal, T. R.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1235-1245.
12. 5. Van Tamelen, E. E.; Curphey, T. J. Tetrahedron Lett. 1962, 121-124. Van Tamelen, E. E.; Storni, A.; Hessler, E. J.; Schwartz, M. A. Bioorg. Chem. 1982, 11, 133-170. A recent paper describes the same transformation in two steps, but with a lower overall yield: Davisson, V. J.; Neal, T. R.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1235-1245.
13. 6. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405-4408.
14. 7. Debal, A.; Cuvigny, T.; Larchevêque, M. Synthesis 1976, 391-393.
15. 8. For some other preparations, see: Fray, M. J.; Jones, R. H.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1985, 2753-2761. Shiao, M.-J.; Yang, C.-Y.; Lee, S.-H.; Wu, T.-C. Synth. Commun. 1988, 18, 359-366. Sodeoka, M.; Yamada, H.; Shibasaki, M. J. Am. Chem. Soc. 1990, 112, 4906-4911. Aszodi, J.; Bonnet, A.; Teutsch, G. Tetrahedron 1990, 46, 1579-1586. Taylor, E. C.; Goswami, S. Tetrahedron Lett. 1991, 32, 7357-7360.
16. 8. For some other preparations, see: Fray, M. J.; Jones, R. H.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1985, 2753-2761. Shiao, M.-J.; Yang, C.-Y.; Lee, S.-H.; Wu, T.-C. Synth. Commun. 1988, 18, 359-366. Sodeoka, M.; Yamada, H.; Shibasaki, M. J. Am. Chem. Soc. 1990, 112, 4906-4911. Aszodi, J.; Bonnet, A.; Teutsch, G. Tetrahedron 1990, 46, 1579-1586. Taylor, E. C.; Goswami, S. Tetrahedron Lett. 1991, 32, 7357-7360.
17. 8. For some other preparations, see: Fray, M. J.; Jones, R. H.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1985, 2753-2761. Shiao, M.-J.; Yang, C.-Y.; Lee, S.-H.; Wu, T.-C. Synth. Commun. 1988, 18, 359-366. Sodeoka, M.; Yamada, H.; Shibasaki, M. J. Am. Chem. Soc. 1990, 112, 4906-4911. Aszodi, J.; Bonnet, A.; Teutsch, G. Tetrahedron 1990, 46, 1579-1586. Taylor, E. C.; Goswami, S. Tetrahedron Lett. 1991, 32, 7357-7360.
18. 8. For some other preparations, see: Fray, M. J.; Jones, R. H.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1985, 2753-2761. Shiao, M.-J.; Yang, C.-Y.; Lee, S.-H.; Wu, T.-C. Synth. Commun. 1988, 18, 359-366. Sodeoka, M.; Yamada, H.; Shibasaki, M. J. Am. Chem. Soc. 1990, 112, 4906-4911. Aszodi, J.; Bonnet, A.; Teutsch, G. Tetrahedron 1990, 46, 1579-1586. Taylor, E. C.; Goswami, S. Tetrahedron Lett. 1991, 32, 7357-7360.
19. 8. For some other preparations, see: Fray, M. J.; Jones, R. H.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1985, 2753-2761. Shiao, M.-J.; Yang, C.-Y.; Lee, S.-H.; Wu, T.-C. Synth. Commun. 1988, 18, 359-366. Sodeoka, M.; Yamada, H.; Shibasaki, M. J. Am. Chem. Soc. 1990, 112, 4906-4911. Aszodi, J.; Bonnet, A.; Teutsch, G. Tetrahedron 1990, 46, 1579-1586. Taylor, E. C.; Goswami, S. Tetrahedron Lett. 1991, 32, 7357-7360.
20. 1H-NMR on the H-3′ triplet which was at δ 6.09 for 22Z and at δ 6.29 for 22E
21. 10. See also the preceding paper.
22. 2Me singlet was at δ 3.60 for 28aZ, at δ 3.66 for 28bZ, and at δ 3.69 for 28cZ.
23. 12. Krajewski-Bertrand, M.-A.; Milon, A.; Nakatani, Y.; Ourisson, G. Biochim. Biophys. Acta 1992, 1105, 213-220
24. 3Si: C, 74.62; H, 8.50. Found C, 74.4; H, 8.6.
25. 14. Heissler, D.; Ladenburger, C. Tetrahedron 1988, 44, 2513-2521.
26. 15. Ladenburger, C.; Heissler, D. J. Chem. Res. (S) 1991, 330.