Identification and synthesis of new bicyclic acetals from the mountain pine beetle, Dendroctonus ponderosae Hopkins (Col.: Scol.)

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 3, 1996, Pages 363-374

  Francke, W ^a   Schroder F ^a   Philipp, P ^a   Meyer, H ^a   Sinnwell, V ^a   Gries, G ^b  

^a UNIVERSITY OF HAMBURG   (Germany)

^b SIMON FRASER UNIVERSITY   (Canada)

Author keywords

5 ethyl 7 methyl 6,8 doxabicyclo 3.2.1 octane; bicyclic acetals; Dendroctonus ponderosae; hydroxybrevicom in

Indexed keywords

5 ETHYL 7 METHYL 6,8 DIOXABICYCLO[3.2.1]OCTANE; BICYCLO COMPOUND; BICYCLO[3.2.1]OCTANE DERIVATIVE; BREVICOMIN; SEX PHEROMONE; UNCLASSIFIED DRUG;

ARTICLE; BEETLE; CHIRALITY; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY;

EID: 0342526821     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(96)00013-2     Document Type: Article

References (24)

1. Silverstein, R. M.; Brownlee, R. G.; Bellas, T. E.; Wood, D. L.; Browne, L. E. Science 1968, 159, 889.
2. Schurig, V.; Weber, R.; Nicholsen, G. J.; Oehlschlager, A. C.; Pierce, Jr. H. D.; Borden, J. H.; Ryker, L. C. Naturwissenschaften 1983, 70, 92.
3. Kinzer, G. W.; Fentiman, Jr, A. F.; Page, Jr, T. E.; Foltz, R. L.; Vité, J. P.; Pitman, G. B. Nature 1969, 221, 477.
4. Stewart, T. E.; Plummer, E. L.; McCandless, L. L.; West, J. R.; Silverstein, R. M. J. Chem. Ecol. 1977, 3, 27.
5. Francke, W.; Bartels, J.; Meyer, H.; Schröder, F.; Kohnle, U.; Baader, E.; Vité, J. P. J. Chem. Ecol. 1995, 21, 1043.
6. Pearce, G. T.; Gore, W. E.; Silverstein, R. M.; Peacock, J. R.; Cuthbert, R. A.; Lanier, G. N.; Simeone, J. B. J. Chem. Ecol. 1975, 1, 115.
7. Pearce, G. T.; Gore, W. E.; Silverstein, R. M. J. Org. Chem. 1976, 41, 2797.
8. Gries, G.; Gries, R.; Borden, J. H.; Pierce, Jr, H. D.; Johnston, B. D.; Oehlschlager, A. C. Naturwissenschaften 1992, 79, 27.
9. Heemann, V.; Francke, W. Naturwissenschaften 1976, 63, 344.
10. Francke, W.; Hindorf, G.; Reith, W. Naturwissenschaften 1979, 66, 619.
11. Gore, W. E.; Pearce, G. T.; Silverstein, R. M. J. Org. Chem. 1976, 41, 607.
12. Wassermann, H. H.; Barber, E. H. J. Am. Chem. Soc. 1969, 91, 3674.
13. Kotsuki, H.; Kadota, I.; Ochi, M. J. Org. Chem. 1990, 55, 4417.
14. Stowell, J. C.; Keith, D. R.; King, B. T. Org. Synth. 1984, 62, 140.
15. König, W.A.; Gehrcke, B.; Icheln, D.; Evers, P.; Dönnecke, J.; Wang, W. J. Chem. Res. Chromatogr. 1992, 15, 367.
16. Prestwich, G. Pure Appl. Chem. 1989, 61, 551.
17. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Koo, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
18. Mitsunobu, O. Synthesis 1981, 1.
19. Bellas, T. E.; Brownlee, R. G.; Silverstein, R. M. Tetrahedron 1969, 25, 5149.
20. Oehlschlager, A. C.; Johnson, B. D. J. Org. Chem. 1987, 52, 940.
21. Tsuij, J. Synthesis 1984, 369.
22. Baker, R.; Herbert, R. H.; Parton, A. H. J. Chem. Soc., Chem. Commun. 1982, 601.
23. Kitching, W.; Lewis, J. A.; Perkins, M. V.; Drew, R. A. J.; Moore, C. J.; Schurig, V.; König, W. A.; Francke, W. J. Org. Chem. 1989, 54, 3893.
24. Bergström, G.; Tengö, J.; Reith, W.; Francke, W. Z. Naturforsch. 1982, 37c, 1124.