Annulated butanolides by ring closing metathesis of diallyltetronic acid derivatives

Tetrahedron Letters

Volumn 46, Issue 21, 2005, Pages 3657-3660

  Schobert, Rainer ^a   Urbina González, Juan Manuel ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

Metathesis; Microwave; Spiro compounds; Tetronic acid

Indexed keywords

BUTYROLACTONE; FURANONE DERIVATIVE; PALLADIUM COMPLEX; SODIUM DERIVATIVE; TETRONIC ACID DERIVATIVE;

ANNULATION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CLAISEN CONDENSATION; REACTION ANALYSIS; RING CLOSING METATHESIS; STRUCTURE ANALYSIS;

EID: 17844363721     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.152     Document Type: Article

References (28)

1. N.H. Fischer, E.J. Oliver, and H.D. Fischer W. Herz H. Grisebach G.W. Kirby Progress in the Chemistry of Organic Natural Products Vol. 38 1979 Springer New York Chapter 2
2. L.F. Silva Synthesis 2001 671 689
3. N. Abe, R. Onoda, K. Shirahata, T. Kato, M.C. Woods, and Y. Kitahara Tetrahedron Lett. 9 3 1968 369 373
4. T.J. Brocksom, F. Coelho, J. Depres, A.E. Greene, M.E. Freire de Lima, O. Hamelin, B. Hartmann, A. Kanazawa, and Y. Wang J. Am. Chem. Soc. 124 2002 15313 15325
5. R.L. Edwards, D.J. Maitland, C.L. Oliver, M.S. Pacey, L. Shields, and A.J.S. Whalley J. Chem. Soc., Perkin Trans. 1 1999 715 719
6. T. Momose, N. Toyooka, M. Nishio, H. Shinoda, H. Fujii, and H. Yanagino Heterocycles 51 6 1999 1321 1343
7. S. Kotha, K. Mandal, A.C. Deb, and S. Banerjee Tetrahedron Lett. 45 2004 9603 9605
8. M. Prat, M. Moreno-Mañas, and J. Ribas Tetrahedron 44 23 1988 7205 7212
9. M. Moreno-Mañas, M. Prat, J. Ribas, and A. Virgili Tetrahedron Lett. 29 5 1988 581 584
10. S. Kotha, A.C. Deb, and R.V. Kumar Bioorg. Med. Chem. Lett. 15 4 2005 1039 1043
11. J. Tsuji E. Negishi Handbook of Organopalladium Chemistry for Organic Synthesis 2002 John Wiley & Sons 1669
12. R. Schobert, G.J. Gordon, G. Mullen, and R. Stehle Tetrahedron Lett. 45 6 2004 1121 1124
13. +, 5%), 194 (14%), 79 (100%), 41 (29%)
14. M. Sodeoka, R. Sampe, S. Kojima, Y. Baba, N. Morisaki, and Y. Hashimoto Chem. Pharm. Bull. 49 2 2001 206 212
15. +, 4%), 215 (6%), 117 (100%), 104 (35%)
16. +, 10%), 161 (27%), 139 (60%), 55 (100%)
17. +, 2%), 176 (50%), 139 (88%), 55 (100%). Satisfactory microanalyses (C, 0.2; H, 0.1) were obtained for 5a-e
18. H. Tahir, and O. Hindsgaul J. Org. Chem. 65 2000 911 913
19. R. Schobert, and S. Siegfried Synlett 2000 686 687
20. +, 70%), 66 (100%), 54 (49%), 39 (59%)
21. +, 100%), 151 (59%), 124 (42%), 79 (74%). Satisfactory microanalyses (C, 0.2; H, 0.2) were obtained for 7a-c and 9a, b
22. A similar observation has been reported recently for the RCM of 2,3-bisalkenylcyclopentanones to give [5.7]bicycles: K. Michalak, M. Michalak, and J. Wicha Tetrahedron Lett. 46 7 2005 1149 1153
23. L.A. Paquette, J.D. Schloss, I. Efremov, F. Fabris, F. Gallou, J. Méndez-Andino, and J. Yang Org. Lett. 2 9 2000 1259 1261
24. 4 requires C, 65.5; H, 5.5
25. A.E. Sutton, B.A. Seigal, D.F. Finnegan, and M.L. Snapper J. Am. Chem. Soc. 124 2002 13390 13391
26. D. Bourgeois, A. Pancrazi, S.P. Nolan, and J. Prunet J. Organomet. Chem. 643/644 2002 247 252
27. J.C. Sworen, J.H. Pawlowa, W. Case, J. Lever, and K.B. Wagener J. Mol. Cat. A: Chem. 194 2003 69 78
28. S.E. Lehman, J.E. Schwendeman, P.M. O'Donnell, and K.B. Wagener Inorg. Chim. Acta 345 2003 190 198