Studies towards the total synthesis of solanoeclepin A: Synthesis and potato cyst nematode hatching activity of analogues containing the tetracyclic left-hand substructure

Journal of the Chemical Society. Perkin Transactions 1

Volumn 2, Issue 14, 2002, Pages 1701-1713

  Benningshof, Jorg C J ^a   Ijsselstijn, Maarten ^a   Wallner, Sabine R ^a   Koster, Anne L ^a   Blaauw, Richard H ^a   Van Ginkel, Angeline E ^a   BriÈre, Jean FranÇois ^a   Van Maarseveen, Jan H ^a   Rutjes, Floris P J T ^a   Hiemstra, Henk ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; ISOMERS; MATHEMATICAL MODELS; MIXTURES; MOLECULAR STRUCTURE; PHASE TRANSITIONS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

HATCHING AGENT; POTATO CYST NEMATODE HATCHING ACTIVITY; SOLANOECLEPIN; UNSATURATED LACTONE;

UNSATURATED COMPOUNDS;

EID: 0035996949     PISSN: 14727781     EISSN: 13645463     Source Type: Journal    
DOI: 10.1039/b202020n     Document Type: Article

References (49)

1. J.C.J. Benningshof, R.H. Blaauw, A.E. van Ginkel, J.H. van Maarseveen, F.P.J.T. Rutjes, H. Hiemstra J. Chem. Soc., Perkin Trans. 1 2002.
2. R.H. Blaauw, J.-F. Brière, R. de Jong, J.C.J. Benningshof, A.E. van Ginkel, F.P.J.T. Rutjes, J. Fraanje, K. Goubitz, H. Schenk, H. Hiemstra Chem. Commun. 2000, 1463.
3. J.C.J. Benningshof, R.H. Blaauw, A.E. van Ginkel, F.P.J.T. Rutjes, J. Fraanje, K. Goubitz, H. Schenk, H. Hiemstra Chem. Commun. 2000, 1465.
4. R.H. Blaauw, J.-F. Brière, R. de Jong, J.C.J. Benningshof, A.E. van Ginkel, F.P.J.T. Rutjes, J. Fraanje, K. Goubitz, H. Schenk, H. Hiemstra J. Org. Chem. 2001, 66, 233.
5. J.-F. Brière, R.H. Blaauw, J.C.J. Benningshof, A.E. van Ginkel, J.H. van Maarseveen, H. Hiemstra Eur. J. Org. Chem. 2001, 2371.
6. R.H. Blaauw, J.C.J. Benningshof, A.E. van Ginkel, J.H. van Maarseveen, H. Hiemstra J. Chem. Soc., Perkin Trans. 1 2001, 2250.
7. R.H. Grubbs, S. Chang Tetrahedron 1998, 54, 4413.
8. A. Fürstner Angew. Chem., Int. Ed. 2000, 39, 3012.
9. T.M. Trnka, R.H. Grubbs Acc. Chem. Res. 2001, 34, 18.
10. A. Kukuzawa, A. Furusaki, I. Mitsuhiko, T. Masamune J. Chem. Soc., Chem. Commun. 1985, 222.
11. H. Okawara, Y. Nii, A. Miwa, M. Sakakibara Tetrahedron Lett. 1987, 28, 2597.
12. A. Miwa, Y. Nii, H. Okawara, M. Sakakibara Agric. Biol. Chem. 1987, 51, 3459.
13. A. Murai, M. Ohkita, T. Honma, K. Hoshi, N. Tanimoto, S. Araki, A. Fukuzawa Chem. Lett. 1992, 2103.
14. G.A. Kraus, B. Johnston, A. Kongsjahju, G.L. Tylka J. Agric. Food Chem. 1994, 42, 1839.
15. H.W. Lin and C.T. Walsh, in Biochemistry of the Cyclopropyl Group, The Chemistry of the Cyclopropyl Group, eds. S. Patai and Z. Rappoport, Interscience, New York, 1987, ch. 16.
16. H.C. Brown, A.K. Mandal, S.U. Kulkarni J. Org. Chem. 1977, 42, 1844.
17. S. V. Ley, J. Norman, W.P. Griffith, S.P. Marsden Synthesis 1994, 639.
18. J.R. Parikh, W.E. von Doering J. Am. Chem. Soc. 1967, 89, 5505.
19. E.N. Marvell, D. Sturmer, C. Rowell Tetrahedron 1966, 22, 861.
20. N. Mander, S.P. Sethi Tetrahedron Lett. 1983, 24, 5425.
21. W.C. Shakespeare, R.P. Johnson J. Am. Chem. Soc. 1990, 112, 8578.
22. W. R. Roush, J.A. Straub, M.S. VanNieuwenhze J. Org. Chem. 1991, 56, 1636.
23. A.B. Charette, H. Juteau, H. Lebel, C. Molinaro J. Am. Chem. Soc. 1998, 120, 11943.
24. A.B. Charette, H. Lebel Org. Synth. 1998, 76, 86.
25. A. B. Charette, A. Beauchemin Org. React. 2001, 58, 1.
26. W.S. McDonald, C.A. Verbicky, C.K. Zercher J. Org. Chem. 1997, 62, 1215.
27. A.G.M. Barrett, D. Hamprecht, A.J.P. White, D.J. Williams J. Am. Chem. Soc. 1997, 119, 8608.
28. P.J. Garegg, R. Johansson, C. Ortega, B. Samuelsson J. Chem. Soc., Perkin Trans. 1 1982, 681.
29. M. Schlosser, B. Schaub J. Am. Chem. Soc. 1982, 104, 5821.
30. E. Vedejs, T. Fleck, S. Hara J. Org. Chem. 1987, 52, 4637.
31. J.P. Schmit, M. Piraux, J.F. Pilette J. Org. Chem. 1975, 40, 1586.
32. S.R. Schow, T.C. McMorris J. Org. Chem. 1979, 44, 3760.
33. P. Knochel, C.J. Rao Tetrahedron 1993, 49, 29.
34. S.T. Nguyen, L.K. Johnson, R.H. Grubbs, J.W. Ziller J. Am. Chem. Soc. 1992, 114, 3974.
35. J. Huang, E.D. Stevens, S.P. Nolan, J.L. Petersen J. Am. Chem. Soc. 1999, 121, 2674.
36. M. Scholl, S. Ding, C.W. Lee, R.H. Grubbs Org. Lett. 1999, 1, 953.
37. H.P. Jensen, K.B. Sharpless J. Org. Chem. 1974, 39, 2314.
38. E.J. Corey, S. Sarshar, M.D. Azimioara, R.C. Newbold, M.C. Noe J. Am. Chem. Soc. 1996, 118, 7851.
39. H. Feng, Y. Bo, J.D. Altom, E.J. Corey J. Am. Chem. Soc. 1999, 121, 6771.
40. M. Frigerio, M. Santagostino Tetrahedron Lett. 1994, 35, 8019.
41. J.M.J. Tronchet, J. Tronchet, A. Birkhauser Helv. Chim. Acta 1970, 53, 1489.
42. C.A. Broka, B. Ruhland J. Org. Chem. 1992, 57, 4888.
43. M. Fétizon, M. Golfier, J.-M. Louis Tetrahedron 1975, 31, 171.
44. D.B. Dess, J.C. Martin J. Org. Chem. 1983, 48, 4155.
45. N.L. Wendler, D. Taub, R.P. Graber Tetrahedron 1959, 7, 173.
46. B.O. Lindgren, T. Nilsson Acta Chem. Scand. 1973, 27, 888.
47. G.A. Kraus, M.J. Taschner J. Org. Chem. 1980, 45, 1175.
48. J.D. White, T.-S. Kim, M. Nambu J. Am. Chem. Soc. 1997, 119, 103.
49. The hatching activity tests were performed at the HLB Research Centre, Wijster, The Netherlands.