Pure and Applied Chemistry, 2007, Volume 79, No. 2, pp. 181-191, References

Pure Appl. Chem., 2007, Vol. 79, No. 2, pp. 181-191

http://dx.doi.org/10.1351/pac200779020181

Conjugate systems in the construction of heterocycles and quaternary stereocenters

Carlos González-Romero, Pablo Bernal, Fabiola Jiménez, María del Carmen Cruz, Aydeé Fuentes-Benites, Adriana Benavides, Rafael Bautista and Joaquín Tamariz

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prol. Carpio y Plan de Ayala, 11340 México, D.F. Mexico

References

1. (a). W. Carruthers. Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford (1990);
1. (b). F. Fringuelli, A. Taticchi. Dienes in the Diels-Alder Reaction, John Wiley, New York (1990);
1. (c). W. Oppolzer. "Intermolecular Diels-Alder reactions", in Comprehensive Organic Synthesis, B. M. Trost, I. Fleming (Eds.), Vol. 5, Chap. 4.1, p. 315, Pergamon, Oxford (1991);
1. (d). F. Fringuelli, A. Taticchi. The Diels-Alder Reaction: Selected Practical Methods, John Wiley, Chichester (2002).
2. (a). D. L. Boger, S. M. Weinreb. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, San Diego (1987);
2. (b). D. L. Boger. "Heterodiene additions", in Comprehensive Organic Synthesis, B. M. Trost, I. Fleming (Eds.), Vol. 5, Chap. 4.3, p. 451, Pergamon, Oxford (1991).
3. (a). M. E. Jung. "Stabilized nucleophiles with electron deficient alkenes and alkynes", in Comprehensive Organic Synthesis, B. M. Trost, I. Fleming (Eds.), Vol. 4, Chap. 1.1, p. 1, Pergamon, Oxford (1991);
3. (b). P. Pelmutter. Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford (1992).
4. (a). J. V. Greenhill. Chem. Soc. Rev. 6, 277 (1977); (http://dx.doi.org/10.1039/cs9770600277)
4. (b). P. Lue, J. V. Greenhill. Adv. Heterocycl. Chem. 67, 207 (1997); (http://dx.doi.org/10.1016/S0065-2725(08)60072-0)
4. (c). B. Stanovnik, J. Svete. Synlett 1077 (2000);
4. (d). A.-Z. A. Elassar, A. A. El-Khair. Tetrahedron 59, 8463 (2003). (http://dx.doi.org/10.1016/S0040-4020(03)01201-8)
5. P. W. Hickmott. "Electrophilic and nucleophilic substitution and addition reactions of enamines", in The Chemistry of Enamines, Z. Rappoport (Ed.), Vol. 1, Chap. 14, p. 727, John Wiley, Chichester (1994).
6. (a). R. Hernandez, J. M. Sanchez, A. Gomez, G. Trujillo, R. Aboytes, G. Zepeda, R. W. Bates, J. Tamariz. Heterocycles 36, 1951 (1993);
6. (b). A. B. Mandal, A. Gomez, G. Trujillo, F. Mendez, H. A. Jimenez, M. J. Rosales, R. Martinez, F. Delgado, J. Tamariz. J. Org. Chem. 62, 4105 (1997). (http://dx.doi.org/10.1021/jo962403g)
7. A. Zempoalteca, J. Tamariz. Heterocycles 57, 259 (2002).
8. A. Benavides, J. Peralta, F. Delgado, J. Tamariz. Synthesis 2499 (2004).
9. R. Martinez, H. A. Jimenez-Vazquez, J. Tamariz. Tetrahedron 56, 3857 (2000). (http://dx.doi.org/10.1016/S0040-4020(00)00311-2)
10. M. C. Cruz, J. Tamariz. Tetrahedron Lett. 45, 2377 (2004). (http://dx.doi.org/10.1016/j.tetlet.2004.01.073)
11. M. C. Cruz, J. Tamariz. Tetrahedron 61, 10061 (2005). (http://dx.doi.org/10.1016/j.tet.2005.08.015)
12. M. C. Cruz, F. Jimenez, F. Delgado, J. Tamariz. Synlett 749 (2006).
13. A. B. Mandal, F. Delgado, J. Tamariz. Synlett 87 (1998). (http://dx.doi.org/10.1055/s-1998-1571)
14. H. Ucar, K. Van derpooten, S. Cacciaguerra, S. Spampinato, J. P. Stables, P. Depovere, M. Isa, B. Masereel, J. Delarge, J. H. Poupaert. J. Med. Chem. 41, 1138 (1998) and refs. cited therein.
15. O. Diouf, P. Carato, P. Depreux, J. P. Bonte, D. H. Caignard, B. Guardiola-Lemaitre, M. C. Rettori, C. Belzung, D. Lesieur. Bioorg. Med. Chem. Lett. 7, 2579 (1997) and refs. cited therein.
16. (a). J. F. Hartwig. Angew. Chem., Int. Ed. 37, 2046 (1998); (http://dx.doi.org/10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L)
16. (b). X. Mei, A. T. August, C. Wolf. J. Org. Chem. 71, 142 (2006); (http://dx.doi.org/10.1021/jo0518809)
16. (c). S. V. Ley, A. W. Thomas. Angew. Chem., Int. Ed. 42, 5400 (2003); (http://dx.doi.org/10.1002/anie.200300594)
16. (d). S. L. Buchwald, C. Mauger, G. Mignani, U. Scholz. Adv. Synth. Catal. 348, 23 (2006). (http://dx.doi.org/10.1002/adsc.200505158)
17. (a). M. Fiebig, J. M. Pezzuto, D. D. Soejarto, A. D. Kinghorn. Phytochemistry 24, 3041 (1985); (http://dx.doi.org/10.1016/0031-9422(85)80052-2)
17. (b). T.-S. Wu, S.-C. Huang, P.-L. Wu, C.-S. Kuoh. Phytochemistry 52, 523 (1999); (http://dx.doi.org/10.1016/S0031-9422(99)00220-4)
17. (c). H.-J. Knolker, K. R. Reddy. Chem. Rev. 102, 4303 (2002). (http://dx.doi.org/10.1021/cr020059j)
18. (a). B. K. Choudhury and D. P. Chakraborty. Phytochemistry 10, 1967 (1971); (http://dx.doi.org/10.1016/S0031-9422(00)86484-5)
18. (b). D. P. Chakraborty, P. Bhattacharyya, S. Roy, S. P. Bhattacharyya, A. K. Biswas. Phytochemistry 17, 834 (1978). (http://dx.doi.org/10.1016/S0031-9422(00)94258-4)
19. W.-S. Li, J. D. McChesney, F. S. El-Feraly. Phytochemistry 30, 343 (1991). (http://dx.doi.org/10.1016/0031-9422(91)84151-H)
20. A. Chakraborty, B. K. Chowdhury, P. Bhattacharyya. Phytochemistry 40, 295 (1995). (http://dx.doi.org/10.1016/0031-9422(95)00047-B)
21. T. Choshi, T. Sada, H. Fujimoto, C. Nagayama, E. Sugino, S. Hibino. J. Org. Chem. 62, 2535 (1997). (http://dx.doi.org/10.1021/jo962038t)
22. B. Akermark, L. Eberson, E. Jonsson, E. Pettersson. J. Org. Chem. 40, 1365 (1975). (http://dx.doi.org/10.1021/jo00897a048)
23. (a). R. Nagarajan. Glycopeptides Antibiotics, Marcel Dekker, New York (1994);
23. (b). M. Renner, Y.-C. Shen, X.-C. Cheng, P. R. Jensen, W. Frankmoelle, C. A. Kauffman, W. Fenical, E. Labrovsky, J. Clardy. J. Am. Chem. Soc. 121, 11273 (1999); (http://dx.doi.org/10.1021/ja992482o)
23. (c). R. M. Wenger. Prog. Chem. Org. Nat. Prod. 50, 123 (1986).
24. (a). D. A. Evans, J. Bartroli, T. L. Shih. J. Am. Chem. Soc. 103, 2127 (1981); (http://dx.doi.org/10.1021/ja00398a058)
24. (b). M. P. Sibi. Aldrichimica Acta 32, 93 (1999);
24. (c). M. Brenner, D. Seebach. Helv. Chim. Acta 82, 2365 (1999). (http://dx.doi.org/10.1002/(SICI)1522-2675(19991215)82:12<2365::AID-HLCA2365>3.0.CO;2-#)
25. (a). J. R. Gage, W. R. Perrault, T.-J. Poel, R. C. Thomas. Tetrahedron Lett. 41, 4301 (2000); (http://dx.doi.org/10.1016/S0040-4039(00)00631-6)
25. (b). C. Puig, M. I. Crespo, N. Godessart, J. Feixas, J. Ibarzo, J.-M. Jimenez, L. Soca, I. Cardelus, A. Heredia, M. Miralpeix, J. Puig, J. Beleta, J. M. Huerta, M. Lopez, V. Segarra, H. Ryder, J. M. Palacios. J. Med. Chem. 43, 214 (2000). (http://dx.doi.org/10.1021/jm991106b)
26. C. Larksarp, H. Alper. J. Am. Chem. Soc. 119, 3709 (1997). (http://dx.doi.org/10.1021/ja964335l)
27. J. d'Angelo, D. Desmaele, F. Dumas, A. Guingant. Tetrahedron: Asymmetry 3, 459 (1992). (http://dx.doi.org/10.1016/S0957-4166(00)80251-7)
28. (a). B. List. Tetrahedron 58, 5573 (2002); (http://dx.doi.org/10.1016/S0040-4020(02)00516-1)
28. (b). B. List. Chem. Commun. 819 (2006) and refs. cited therein.
29. P. H.-Y. Cheong, H. Zhang, R. Thayumanavan, F. Tanaka, K. N. Houk, C. F. Barbas III. Org. Lett. 8, 811 (2006) and refs. cited therein.
30. (a). P. Melchiorre, K. A. Jorgensen. J. Org. Chem. 68, 4151 (2003); (http://dx.doi.org/10.1021/jo026837p)
30. (b). J. Wang, H. Li, L. Zu, W. Wang. Adv. Synth. Catal. 348, 425 (2006). (http://dx.doi.org/10.1002/adsc.200505420)
31. (a). L. D. Via, E. Uriarte, E. Quezada, A. Dolmella, M. G. Ferlin, O. Gia. J. Med. Chem. 46, 3800 (2003); (http://dx.doi.org/10.1021/jm0210919)
31. (b). A. Versari, N. Natali, M. T. Russo, A. Antonelli. J. Agric. Food Chem. 51, 4978 (2003); (http://dx.doi.org/10.1021/jf030083d)
31. (c). L.-L. Yang, M.-C. Wang, L.-G. Chen, C.-C. Wang. Planta Med. 69, 1091 (2003); (http://dx.doi.org/10.1055/s-2003-45188)
31. (d). K. Gunaydin, S. Savci. Nat. Prod. Res. 19, 203 (2005). (http://dx.doi.org/10.1080/14786410310001630546)
32. (a). J. K. MacLeod, B. R. Worth, R. J. Wells. Tetrahedron Lett. 241 (1972); (http://dx.doi.org/10.1016/S0040-4039(01)84290-8)
32. (b). K. K. Park, J. Jeong. Tetrahedron 61, 545 (2005); (http://dx.doi.org/10.1016/j.tet.2004.11.022)
32. (c). G. Chen, D. J. Yee, N. G. Gubernator, D. Sames. J. Am. Chem. Soc. 127, 4544 (2005). (http://dx.doi.org/10.1021/ja0428457)
33. (a). Y. Zhang, D. Candelaria, J. W. Herndon. Tetrahedron Lett. 46, 2211 (2005); (http://dx.doi.org/10.1016/j.tetlet.2005.02.037)
33. (b). A. Goel, M. Dixit. Synlett 1990 (2004). (http://dx.doi.org/10.1055/s-2004-831180)

Pure and Applied Chemistry

Navigation

PAC Archives

RSS Feeds

Highlights

Conjugate systems in the construction of heterocycles and quaternary stereocenters

References

Pure and Applied Chemistry

Navigation

Search PAC

PAC Archives

RSS Feeds

Highlights

Conjugate systems in the construction of heterocycles and quaternary stereocenters

References