Stereoselective synthesis of (2E,4Z)-dienamides employing (triphenylphosphoranylidene)ketene

European Journal of Organic Chemistry

Volumn , Issue 17, 2009, Pages 2828-2835

  Pachali, Steffen ^a   Hofmann, Christine ^a   Rapp, Georg ^b   Schobert, Rainer ^b   Baro, Angelika ^a   Frey, Wolfgang ^a   Laschat, Sabine ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

Aldehydes; C C coupling; Synthetic methods; Wittig reactions; Ylides

Indexed keywords

EID: 66449114632     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900176     Document Type: Article

References (52)

1. Review: a) S. E. Binns, J. F. Livesey, J. T. Arnason, B. R. Baum, J. Agrie, Food Chem. 2002, 50, 3673-3687;
2. b) R. Martin, H. Becker, Phytochemistry 1985, 24, 2295-2300.
3. Y. Chen, T. Fu, T. Tao, J. Yang, Y. Chang, M. Wang, L. Kim, L. Qu, J. Cassady, R. Scalzo, X. Wang, J. Nat. Prod, 2005, 68, 773-776.
4. a) N. B. Cech, K. Tutor, B. A. Doty, R. Spelman, M. Sasagawa, G. M. Raner, C. A. Wenner, Planta Med. 2006, 72, 1372-1377;
5. b) S. E. Binns, B. Purgina, C. Bergeron, M. L. Smith, L. Bail, B. R. Baum, J. T. Arnason, Planta Med. 2000, 66, 241-244.
6. J. P. Ley, J.-M. Hilmer, B. Weber, G. Krammer, I. L. Gatfield, H.-J. Bertram, Eur. J. Org. Chem. 2004, 5135-5140.
7. B. S. Siddiqui, S. Begum, T. Gulzar, F. Noor, Phytochemistry 1997, 45, 1617-1619.
8. T. Yoshida, M. Murai, M. Abe, N. Ichimaru, T. Harada, T. Nishioka, H. Miyoshi, Biochemistry 2007, 46, 10365-10372.
9. J. Kobayashi, F. Itagaki, H. Shigemori, T. Sasaki, J. Nat. Prod. 1993, 56, 976-981.
10. S. Kanazawa, N. Fusetani, S. Matsunaga, Tetrahedron Lett. 1993, 34, 1065-1068.
11. N. Cramer, S. Helbig, A. Baro, S. Laschat, R. Diestel, F. Sasse, D. Mathieu, C. Richter, G. Kummerlöwe, B. Luy, H. Schwalbe, ChemBioChem 2008, 9, 2474-2486.
12. [10]a) M.-A. Bae, K. Yamada, Y. Ijuin, T. Tsuji, K. Yazawa, Y. Tomono, D. Uemura, Heterocyel. Commun. 1996, 2, 315-318;
13. b) B. Myong-Ae, K. Yamada, D. Uemura, J. H. Sen, Y. H. Kim, J. Microbiol. Biotechnol. 1998, 8, 455-460;
14. c) K. Yamada, M. Ruramoto, D. Uemura, Recent Res. Devol. Pure Appl. Chem. 1999, 3, 245-254.
15. a) L. O. Ruzo, S. J. Holloway, J. E. Casida, V. V. Krishnamurthy, J. Agrie. Food Chem. 1988, 36, 841-844;
16. b) M. Elliott, A. W Farnham, N. F. Janes, D. M. Johnson, D. A. Pulman, Pestic. Sci. 1987, 18, 239-244;
17. c) M. Elliott, A. W Farnham, N. F. Janes, D. M. Johnson, D. A. Pulman, Pestic. Sci. 1987, 18, 229-238.
18. a) F. Bohlmann, C. Zdero, Chem. Ber. 1973, 106, 1328-1336;
19. b) F. Bohlmann, R. Miethe, Chem. Ber. 1967, 100, 3861-3868.
20. 11b] and: a) U. Kazmaier, Chem. Commun. 1997, 2305-2306;
21. b) F. Bohlmann, M. Ganzer, M.Krüger, E. Nordhoff, Tetrahedron 1983, 39, 123-128.
22. Y-Z. Huang, X.-S. Mo, Synlett 1998, 93-95.
23. M. A. Blaskovich, M. Kahn, J. Org. Chem. 1998, 63, 1119-1125.
24. First generation synthesis: a) N. Cramer, M. Buchweitz, S. Laschat, W. Frey, A. Baro, D. Mathieu, C. Richter, H. Schwalbe, Chem. Eur. J. 2006, 12, 2488-2503;
25. b) N. Cramer, S . Laschat, A. Baro, H. Schwalbe, C. Richter, Angew. Chem. 2005, 117, 831-833;
26. Angew. Chem. Int. Ed. 2005, 44, 820-822.
27. For a different approach see: A. C. Hart, A. J Phillips, J. Am. Chem. Soc, 2006, 128, 1094-1095.
28. a) H.J. Bestmann, W. Kellermann, Synthesis 1994, 1257-1261;
29. b) H. J. Bestmann, M. Schmidt, R. Schobert, Synthesis 1988, 49-53;
30. c) H. J. Bestmann, R. Schobert, Angew. Chem. 1985, 97, 783-784;
31. Angew. Chem. Int. Ed. Engl. 1985, 24, 791-792;
32. d) H. J. Bestmann, D. Sandmeier, Angew. Chem. 1975, 87, 630;
33. Angew. Chem. Int. Ed. Engl. 1975, 14, 634.
34. a) R. Schobert, A. Stangl, Tetrahedron Lett. 2005, 46, 1127-1130;
35. b) R. Schobert, C. Jagusch, C. Melanophy, G. Mullen, Org. Biomol. Chem. 2004, 2, 3524-3529;
36. c) R. Schobert, S. Siegfried, G. J. Gordon, J. Chem. Soc. Perkin Trans. 1 2001, 2393-2397.
37. For related work see: a) R. K. Boeckman Jr., X. Song, J. E. Pero, J. Org. Chem. 2006, 71, 8969-8972;
38. b) J. Westman, K. Orrling, Comb. Chem. High Throughput Screening 2002, 5, 571-574.
39. Enantiomeric excesses were determined by capillary GC using a chiral-phase Amidex C (for 12c) or Bondex un-α (for 12d).
40. S.-I. Hashimoto, S.-I. Yamada, K. Koga, Chem. Pharm. Bull. 1979, 27, 771-782.
41. a) I. Vaulont, H.-J. Gais, N. Reuter, E. Schmitz, R. R. L. Ossenkamp, Eur. J. Org. Chem. 1.998, 805-826;
42. b) T. Anderl, M. Emo, S. Laschat, A. Baro, W. Frey, Synthesis 2008, 1619-1627.
43. M. J. Robins, J. S. Wilson, J. Am. Chem. Soc. 1981, 103, 932-933.
44. A. P. Marchand, V. S. Kumar, H. R. Hariprakasha, J. Org. Chem. 2001, 66, 2072-2077.
45. K. Ando, J. Org. Chem. 1997, 62, 1934-1939.
46. P. A. Jacobi, J. I. Kravitz, W. Zheng, J. Org. Chem. 1995, 60, 376-385.
47. H. J Bestmann, K. Roth, M. Ettlinger, Chem. Ber. 1982, 115, 161-171.
48. R. A. Doohan, J. J. Hannan, N. W. A. Geraghty, Org. Biomol. Chem. 2006, 4, 942-952.
49. R. Schobert, R. K. Boeckman Jr., J. E. Pero, Org. Synth. 2005, 82, 140-143.
50. L. Gros, S. O. Lorente, C. J. Jimenez, V. Yardley, L. Rattray, H. Wharton, S. Little, S. L. Croft, L. M. Ruiz-Perez, D. GonzalezPacanowska, I. H. Gilbert, J. Med. Chem. 2006, 49, 6094-6103.
51. CCDC-711596 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data. - request/cif.
52. P. Stanetty, M. Kremslehner, Tetrahedron Lett. 1998, 39, 811-812.