Preparation of (2E,6E)-10,11-dihydrofamesol via a (bisphenyl)dithioacetal reduction

Tetrahedron Letters

Volumn 39, Issue 52, 1998, Pages 9609-9612

  Mechelke, Mark F ^a   Wiemer, David F ^a  

^a E11 SSH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(BISPHENYL)DITHIOACETAL; 10,11 DIHYDROFARNESOL; 2 PROPANOL; ACETAL DERIVATIVE; FARNESOL; UNCLASSIFIED DRUG;

ARTICLE; REDUCTION; SYNTHESIS;

EID: 0032564636     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02201-1     Document Type: Article

References (28)

1. 1. Willumsen, B. M.; Norris, K.; Papageorge, A. G.; Hubbert, N. L.; Lowy, D. R. EMBO J. 1984, 3, 2581.
2. 2. Jackson, J. H.; Cochrane, C. G.; Bourne, J. R.; Solski, P. A.: Buss, J. E.; Der, C. J. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 3042.
3. 3. Hancock, J. F.; Magee, A. I.; Childs, J. E.; Marshall, C. J. Cell 1989, 57, 1167
4. 4. Barbacid, M. Ann. Rev. Biochem. 1987, 56, 779.
5. 5. Zahn, T. J.; Ksebati, M. B.; Gibbs, R. A. Tetrahedron Lett. 1998, 39, 3991.
6. 6. a) Gibbs, R. A.; Krishnan, U.; Dolence, J. M.; Poulter, C. D. J. Org. Chem. 1995, 60, 7821.
7. b) Mu, Y. Q.; Gibbs, R. A.; Eubanks, L. M.; Poulter, C. D. J. Org. Chem. 1996, 61, 8010.
8. 7. Park, H.; Boduluri, S .R.; Moomaw, J. F.; Casey, P. J.; Beese, L. S. Science 1997, 275, 1800.
9. 8. Mechelke, M. F.; Wiemer, D. F. Tetrahedron Lett. 1998, 39, 783.
10. 9. Eidem, A.; Buchecker, R.; Kjosen, H.; Liaaen-Jensen, S. Acta Chem. Scand. B 1975, 29, 1015.
11. 10. Washburn, W.; Kow, R. Tetrahedron Lett. 1977, 1555.
12. 11. Zhang, H.; Chen, J.; Jiang, J. Yingyong Huaxue 1993, 10, 104. This approach gave a 1.3:1.0 ratio of 6E:6Z isomers in our hands.
13. 12. Biller, S. A. U.S. Patent, Patent Number 5,212,164, May 18, 1993.
14. 13. Hohl, R. J.; Lewis, K. A.; Cermak, D. M.; Wiemer, D. F. Lipids 1998, 33, 39.
15. 14. Sato, K.; Inoue, S.; Onishi, A.; Uchida, N.; Minowa, N. J. Chem. Soc., Perkin Trans, 1 1981, 761.
16. 15. Corey, E. J.; Achiwa, K. J. Org. Chem. 1969, 34, 3667.
17. 1H NMR analysis.
18. 17. Tamao, K.; Ishida, N.; Kumada, M. J. Org. Chem. 1983, 48, 2122.
19. 18. a) Kodama, M.; Takahashi, T.; Kojima, T.; Ito, S. Tetrahedron Lett. 1982, 23, 3397.
20. b) Fujita, Y.; Ishiguro, M.; Onishi, T.; Nishida, T. Bull. Chem. Soc. Jpn. 1982, 55, 1325.
21. c) Hashimoto, M.; Kan, T.; Yanagiya, M.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1987, 28, 5665.
22. 19. Dauben, W. G.; Saugier, R. K.; Fleischhauer, I. J. Org. Chem. 1985, 50, 3767.
23. 20. a) Biellmann, J. F.; Ducep, J. B. Tetrahedron Lett. 1969, 3707.
24. b) Biellmann, J. F.; Ducep, J. B. Tetrahedron 1971, 27, 5861.
25. 21. Dolak, T. M.; Bryson, T. A. Tetrahedron Lett. 1977, 1961.
26. 22. Takeda, T.; Watanabe, M.; Nozaki, N.; Fujiwara, T. Chem. Lett. 1998, 115.
27. 23. Armstrong, R. J.; Weiler, L. Can. J. Chem. 1983, 61, 2530.
28. 12 2 without further purification (643 mg, 98%).