Synthesis of farnesol isomers via a modified wittig procedure

Organic Letters

Volumn 7, Issue 22, 2005, Pages 4803-4806

  Yu, José S ^a   Kleckley, Troy S ^a   Wiemer, David F ^a  

^a E11 SSH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FARNESOL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; ORGANIC CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CHEMISTRY, ORGANIC; FARNESOL; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 27644439968     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0513239     Document Type: Article

References (18)

1. Liang, P. H.; Ko, T. P.; Wang, A. H. Eur. J. Biochem. 2002, 269, 3339-3354.
2. Shchepin, R.; Hornby, J. M.; Burger, E.; Niessen, T.; Dussault, P.; Nickerson, K. W. Chem. Biol. 2003, 10, 743-750.
3. Xie, H.; Shao, Y.; Becker, J. M.; Naider, F.; Gibbs, R. A. J. Org. Chem. 2000, 65, 8552-8563 and references therein.
4. Inoue, Y,; Shiraishi, A.; Hada, T.; Hirose, K.; Hamashima, H.; Shimada, J. FEMS Microbiol. Lett. 2004, 237, 325-331.
5. Hohl, R. J.; Lewis, K. A.; Cermak, D. M.; Wiemer, D. F. Lipids 1998, 33, 39-46.
6. Downward, J. Curr. Opin. Genet. Dev. 1998, 8, 49-54.
7. (a) Shao, Y.; Eummer, J. T.; Gibbs, R. A. Org. Lett. 1999, 1, 627-630.
8. (b) Zahn, T. J.; Whitney, J.; Weinbaum, C.; Gibbs, R. A. Bioorg. Med. Chem. Lett. 2001, 11, 1605-1608.
9. Cane, D. E.; Iyengar, R.; Shiao, M. S. J. Am. Chem. Soc. 1981, 103, 914-931.
10. Krigman, M. R.; Silverman, A. P. Neurotoxicology 1984, 5, 129-139.
11. Schlosser, M.; Coffinet, D. Synthesis 1972, 575-576.
12. Corey, E. J.; Yamamoto, H. J. J. Am. Chem. Soc. 1970, 92, 6636-6637.
13. Representative experimental procedures and additional spectral data are available in Supporting Information.
14. Schlosser, M.; Jenny, T.; Guggisberg, Y. Synlett 1990, 11, 704.
15. Kato, T.; Suzuki, M.; Kobayashi, T.; Moore, B. P. J. Org. Chem. 1980, 45, 1126-1130.
16. Coates, R. M.; Ley, D. A.; Cavender, P. L. J. Org. Chem. 1978, 43, 4915-4922.
17. Commercial trans,trans-farnesol contained only ∼70% of the desired isomer via GC analysis.
18. Burrell, J. W. K.; Garwood, R. F.; Jackman, L. M.; Oskay, E.; Weedon, B. C. L. J. Chem. Soc. C 1966, 2144-2154.