First asymmetric synthesis of (+)-sordidin and (-)-7-epi-sordidin, aggregation pheromones of the banana weevil cosmopolites sordidus

European Journal of Organic Chemistry

Volumn , Issue 13, 2005, Pages 2677-2683

  Enders, Dieter ^a   Breuer, Irene ^a   Nühring, Anja ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric synthesis; Epoxide opening; Pheromones; Quaternary stereocenters; SAMP RAMP Hydrazones

Indexed keywords

EID: 22144476187     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500112     Document Type: Article

References (29)

1. H. E. Ostmark, Annu. Rev. Entomol. 1974, 19, 161.
2. W. J. Budenberg, I. O. Ndiege, F. W. Karago, J. Chem. Ecol. 1993, 19, 1905.
3. J. Beauhaire, P.-H. Ducrot, C. Malosse, D. Rochat, I. O. Ndiege, D. O. Otieno, Tetrahedron Lett. 1995, 36, 1043.
4. J. Beauhaire, P.-H. Ducrot, Bioorg. Med. Chem. 1996, 4, 413.
5. P.-H. Ducrot, Synth. Commun. 1996, 26, 3923.
6. I. O. Ndiege, S. Jayaraman, A. C. Oehlschlager, L. Gonzalez, D. Alpizar, M. Fallas, Naturwissenschaften 1996, 83, 280.
7. T. Nakayama, K. Mori, Liebigs Ann./Recueil 1997, 1075.
8. M. T. Fletcher, C. J. Moore, W. Kitching, Tetrahedron Lett. 1997, 38, 3475.
9. a) D. J. Wardrop, R. E. Forslund, Tetrahedron Lett. 2002, 43, 737;
10. b) D. J. Wardrop, R. E. Forslund, C. L. Landrie, A. I. Velter, D. Wink, B. Surve, Tetrahedron: Asymmetry 2003, 14, 929.
11. a) D. Enders, in: Asymmetric Synthesis, vol. 3B (Ed.: J. D. Morrison), Academic Press, Orlando, 1984;
12. b) D. Enders, M. Klatt, in: Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, New York, 1995;
13. c) D. Enders, A. Job, C. F. Janeck, W. Bettray, R. Peters, Tetrahedron 2002, 58, 2253.
14. D. Enders, B. Bockstiegel, Synthesis 1989, 493.
15. Review: D. Enders, M. Voith, A. Lenzen, Angew. Chem. 2005, 117, 1330;
16. Angew. Chem. Int. Ed. 2005, 44, 1304.
17. a) U. Jegelka, Dissertation, RWTH Aachen, 1992;
18. b) D. Enders, U. Jegelka, Tetrahedron Lett. 1993, 34, 2453.
19. a) D. Enders, A. Nühring, J. Runsink, G. Raabe, Synthesis 2001, 1406;
20. b) A. Nühring, Dissertation, RWTH Aachen, 2001.
21. a) D. H. R. Barton, S. W. McCombie, J. Chem. Soc., Perkin Trans. 1 1975, 1574;
22. b) W. Hartwig, Tetrahedron 1983, 39, 2609;
23. c) W. B. Motherwell, D. Crich, in: Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992.
24. A. G. Myers, L. McKinstry, J. Org. Chem. 1996, 61, 2428.
25. K. Mori, T. Nakayama, H. Takikawa, Tetrahedron Lett. 1996, 37, 3741.
26. a) D. Enders, P. Fey, H. Kipphardt, Org. Synth. 1987, 65, 173;
27. b) D. Enders, P. Fey, H. Kipphardt, Org. Synth. 1987, 65, 183.
28. D. Hoppe, H. Schmincke, H.-W. Kleemann, Tetrahedron 1989, 45, 687.
29. D. S. Connor, G. W. Klein, G. N. Taylor, Org. Synth. 1972, 52, 16.