Sila-linalool as a pheromone analogue: A study on C/Si bioisosterism

Organometallics

Volumn 22, Issue 2, 2003, Pages 370-372

  Tacke, Reinhold ^a   Schmid, Thomas ^a   Hofmann, Matthias ^a   Tolasch, Till ^b   Francke, Wittko ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF HAMBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM COMPOUNDS; ELECTROPHYSIOLOGY; SILICON; SYNTHESIS (CHEMICAL);

ELECTROANTENNOGRAPHY;

ORGANIC COMPOUNDS;

EID: 0037455587     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020703k     Document Type: Article

References (23)

1. Recent publications dealing with C/Si bioisosterism: (a) Tacke, R.; Reichel, D.; Jones, P. G.; Hou, X.; Waelbroeck, M.; Gross, J.; Mutschler, E.; Lambrecht, G. J. Organomet. Chem. 1996, 521, 305-323.
2. (b) Tacke, R.; Merget, M.; Bertermann, R.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497.
3. (c) Merget, M.; Günther, K.; Bernd, M.; Günther, E.; Tacke, R. J. Organomet. Chem. 2001, 628, 183-194.
4. (d) Tacke, R.; Kornek, T.; Heinrich, T.; Burschka, C.; Penka, M.; Pülm, M.; Keim, C.; Mutschler, M.; Lambrecht, G. J. Organomet. Chem. 2001, 640, 140-165.
5. (e) Tacke, R.; Handmann, V. I.; Kreutzmann, K.; Keim, C.; Mutschler, E.; Lambrecht, G. Organometallics 2002, 21, 3727-3732.
6. (f) Tacke, R.; Handmann, V. I.; Bertermann, R.; Penka, M.; Seyfried, C. Organometallics, in press.
7. (a) Wrobel, D.; Tacke, R.; Wannagat, U.; Harder, U. Chem. Ber. 1982, 115, 1694-1704.
8. (b) Tacke, R.; Wiesenberger, F. Z. Naturforsch., B 1991, 46, 275-279.
9. (c) Tacke, R.; Schmid, T.; Burschka, C.; Penka, M.; Surburg, H. Organometallics 2002, 21, 113-120.
10. Wrobel, D.; Wannagat, U. Liebigs Ann. Chem. 1982, 734-738.
11. (a) Bergström, G.; Tengö, J. J. Chem. Ecol. 1978, 4, 437-449.
12. (b) Hefetz, A.; Batra, S. W. T.; Blum, M. S. Experientia 1979, 35, 319-320.
13. (c) Cane, J. H.; Tengö, J. O. J. Chem. Ecol. 1981, 7, 427-436.
14. (d) Borg-Karlson, A.-K.; Unelius, C. R.; Valterová, I.; Nilsson, L. A. Phytochemistry 1996, 41, 1477-1483.
15. (e) Borg-Karlson, A.-K.; Tengö, J.; Valterová, I.; Unelius, C. R.; Taghizadeh, T.; Tolasch, T.; Francke, W. J. Chem. Ecol., in press.
16. Review dealing with the topic "chirality in bioorganosilicon chemistry": Tacke, R.; Wagner, S. A. In The Chemistry of Organosilicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, U.K., 1998; Vol. 2, Part 3, pp 2363-2400.
17. For an alternative synthesis of rac-1b, see ref 3.
18. Publications dealing with the chromatographic separation of chiral organosilicon compounds, with the silicon atom as the center of chirality: (a) Tacke, R.; Reichel, D.; Günther, K.; Merget, S. Z. Naturforsch., B 1995, 50, 568-572.
19. (b) Reference 1c.
20. For a detailed description of this method, see: Bjostad, L. B. In Methods in Chemical Ecology; Millar, J. G., Haynes, K. F., Eds.; Kluwer Acad. Publ.: Boston, MA, 1998; Vol. 1, pp 339-375.
21. Arsequell, G.; Camps, F.; Fabriàs, G.; Guerrero, A. Tetrahedron Lett. 1990, 31, 2739-2742.
22. Tacke, R.; Linoh, H.; Ernst, L.; Moser, U.; Mutschler, E.; Sarge, S.; Cammenga, G.; Lambrecht, G. Chem. Ber. 1987, 120, 1229-1237.
23. Biernacki, W.; Gdula, A. Synthesis 1979, 37-38.