Stereoisomer libraries: Total synthesis of all 16 stereoisomers of the pine sawfly sex pheromone by a fluorous mixture-synthesis approach

Proceedings of the National Academy of Sciences of the United States of America

Volumn 101, Issue 33, 2004, Pages 12008-12012

  Dandapani, Sivaraman ^a   Jeske, Mario ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,7,11 TRIMETHYLUNDECANOL PROPANOATE ESTER; PROPIONIC ACID DERIVATIVE; SEX PHEROMONE; UNCLASSIFIED DRUG; UNDECANOL;

ARTICLE; DIASTEREOISOMER; FLY; HORMONE SYNTHESIS; NONHUMAN; PINE SAWFLY; PRIORITY JOURNAL; SPECTRAL SENSITIVITY; STEREOISOMERISM; STRUCTURE ANALYSIS; TECHNIQUE;

ANIMALS; CHEMISTRY, ORGANIC; FEMALE; FLUORINE; HYMENOPTERA; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SEX ATTRACTANTS; STEREOISOMERISM;

EID: 4344596714     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0401677101     Document Type: Article

References (20)

1. Luo, Z. Y., Zhang, Q. S., Oderaotoshi, Y. & Curran, D. P. (2001) Science 291, 1766-1769.
2. Curran, D. P. & Oderaotoshi, Y. (2001) Tetrahedron 57, 5243-5253.
3. Curran, D. P. & Furukawa, T. (2002) Org. Lett. 4, 2233-2235.
4. Zhang, W., Luo, Z., Chen, C. H. T. & Curran, D. P. (2002) J. Am. Chem. Soc. 124, 10443-10450.
5. Zhang, Q. S., Rivkin, A. & Curran, D. P. (2002) J. Am. Chem. Soc. 124, 5774-5781.
6. Zhang, Q. S., Lu, H. J., Richard, C. & Curran, D. P. (2004) J. Am. Chem. Soc. 126, 36-37.
7. Houghten, R. A., Pinilla, C., Appel, J. R., Blondelle, S. E., Dooley, C. T., Eichler, J., Nefzi, A. & Ostresh, J. M. (1999) J. Med. Chem. 42, 3743-3778.
8. An, H. Y. & Cook, P. D. (2000) Chem. Rev. (Washington, D.C.) 100, 3311-3340.
9. Curran, D. P. (2001) Synlett, 1488-1496.
10. Larsson, M., Nguyen, B.-V., Högberg, H.-E. & Hedenström, E. (2001) Eur. J. Org. Chem., 353-363.
11. Bergström, G., Wassgren, A.-B., Anderbrandt, O., Ochieng, S. A., Östrand, F., Hansson, B. S., Hedenström, E. & Höberg, H.-E. (1998) Naturwissenschaften 85, 244-248.
12. Hedenström, E. & Andersson, F. (2002) J. Chem. Ecol. 28, 1237-1254.
13. Nakamura, Y. & Mori, K. (1999) Eur. J. Org. Chem. 2175-2182.
14. White, J. D., Theramongkol, P., Kuroda, C. & Engebrecht, J. R. (1988) J. Org. Chem. 53, 5909-5913.
15. Oppolzer, W., Blagg, J., Rodriguez, I. & Walther, E. (1990) J. Am. Chem. Soc. 112, 2767-2769.
16. Dandapani, S. (2004) Ph.D. thesis (University of Pittsburgh, Pittsburgh).
17. Tsunoda, T., Suzuki, M. & Noyori, R. (1980) Tetrahedron Lett. 21, 1357-1360.
18. Ishihara, K., Mori, A. & Yamamoto, H. (1990) Tetrahedron 46, 4595-4599.
19. Blakemore, P. R. (2002) J. Chem. Soc. Perkin Trans. 1, 2563-2579.
20. Booth, R. J. & Hodges, J. C. (1997) J. Am. Chem. Soc. 119, 4882-4887.