MIRC reactions using sulfoxides and synthesis of dictyopterene A

Arkivoc

Volumn 2002, Issue 6, 2002, Pages 91-103

  Casey, Mike ^a   Keaveney, Claire M ^a   Walker, Andrew J ^b  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b UNIVERSITY OF SALFORD   (United Kingdom)

Author keywords

Conjugate addition; Dictyopterene A; MIRC reactions; Sulfoxides

Indexed keywords

1 (1 HEXENYL) 2 VINYLCYCLOPROPANE; CARBOXYLIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; HEXYL 1 METHYL 2 IMIDAZOLYL SULFOXIDE; METHYL 2 (2 PHENYLETHENYL)CYCLOPROPANECARBOXYLATE; METHYL 2 [1 (1 METHYL 2 IMIDAZOLYLSULFINYL) 2 PHENYLETHYL]CYCLOPROPANECARBOXYLATE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; ELIMINATION REACTION; ISOMERISM; MICHAEL ADDITION; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS; THERMAL ANALYSIS;

EID: 3242779413     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. Little, R. D.; Dawson, J. R. Tetrahedron Lett. 1980, 21, 2609.
2. Caine, D. Tetrahedron, 2001, 57, 2643.
3. (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961.
4. (b) Carreño, M. C. Chem. Rev. 1995, 95, 1717.
5. (c) Wang, C. C.; Huang, H. C.; Reitz, D. B. Org. Prep. Proced. Intl. 2002, 34, 271.
6. Ghera, E.; Ben-David, Y. Tetrahedron Lett. 1979, 4603.
7. (a) Toru, T.; Nakamura, Takemoto, H.; Ueno, Y. Synlett 1997, 449.
8. (b) Nakamura, S.; Watanabe, Y.; Toru, T. J. Chem. Soc., Perkin Trans. 1 1990, 3403.
9. (a) Casey, M.; Manage, A. C.; Nezhat, L. Tetrahedron Lett. 1988, 29, 5821.
10. (b) Casey, M.; Manage, A. C.; Gairns, R. S. Tetrahedron Lett. 1989, 30, 6919.
11. (c) Casey, M.; Gairns, R. S.; Geraghty, G. M.; Kelly, C. J.; Murphy, P. J.; Walker, A. J. Synlett 2000, 1721.
12. (d) Appelbe, Z.; Casey, M.; Keaveney, C.; Kelly, C. J.; Synlett 2002, in press.
13. (a) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965.
14. (b) Casey, M.; Gairns, R. S.; Walker, A. J. Synlett 2000, 1725.
15. (a) Desmaële, D.; Louvet, J.-M. Tetrahedron Lett. 1994, 35, 2549.
16. (b) Zhou, Z.; Larouche, D.; Bennett, S. M. Tetrahedron 1995, 51, 11623.
17. Moore, R. E.; Pettus, J. A. Jr. Tetrahedron Lett. 1968, 4787.
18. (b) Moore, R. E.; Pettus, J. A. Jr.; Mistysyn, J. J. Org. Chem. 1974, 39, 2201.
19. (a) Ohloff, G.; Pickenhagen, W. Helv. Chim. Acta 1969, 52, 880.
20. (b) Das, K. C.; Weinstein, B. Tetrahedron Lett. 1969, 3459.
21. (c) Jaenicke, L.; Akintobi, T.; Marner, F.-J. Liebigs Ann. Chem. 1973, 1252.
22. (d) Billups, W. E.; Chow, W. Y.; Cross, J. H. J. Chem. Soc., Chem. Commun. 1974, 252.
23. (e) Akintobi, T.; Jaenicke, L.; Marner, F.-J.; Waffenschmidt, S. Liebigs Ann. Chem. 1979, 986.
24. (f) Kajiwara, T.; Nakatomi, T.; Sasaki, Y.; Hatanaka, A. Agric. Biol. Chem. 1980, 44, 2099.
25. (g) Yamada, K.; Tan, H.; Hirota, K. Tetrahedron Lett. 1980, 21, 4873.
26. (h) Colobert, F.; Genet, J.-P. Tetrahedron Lett. 1985, 26, 2779.
27. (i) Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron 1991, 47, 1215.
28. (j) Narjes, F.; Bolte, O.; Icheln, D.; König, W. A.; Schaumann, E. J. Org. Chem. 1993, 58, 626.
29. (k) Itoh, T.; Inoue, H.; Emoto, S. Bull. Chem. Soc. Jpn. 2000, 73, 409.
30. Pitchen, P.; France, C. J.; McFarlane, I. M.; Newton, C. G.; Thompson, D. M. Tetrahedron Lett. 1994, 35, 485.
31. Cotton, H.; Elebring, T.; Larsson, M.; Li, L.; Sörensen, H.; von Unge, S. Tetrahedron: Asymmetry 2000, 11, 3819.
32. Woods, G. F., Jr. Org. Synth. 1955, coll. Vol. 3, 470.
33. Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071.