Enantioselective catalysis on the solid phase: Synthesis of natural product-derived tetrahydropyrans employing the enantioselective oxa-Diels-Alder reaction

Advanced Synthesis and Catalysis

Volumn 348, Issue 12-13, 2006, Pages 1511-1515

  Sanz, Miguel A ^a,b   Voigt, Tobias ^a,b   Waldmann, Herbert ^a,b  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Combinatorial chemistry; Enantioselectivity; Oxa Diels Alder reaction; Solid phase synthesis; Tetrahydropyrans

Indexed keywords

EID: 33748268305     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606026     Document Type: Article

References (34)

1. a) R. Breinbauer, I. R. Vetter, H. Waldmann, Angew. Chem. 2002, 114, 3002-3015;
2. Angew. Chem. Int. Ed. 2002, 41, 2878-2890;
3. b) M. A. Koch, H. Waldmann, Drug Disc. Today 2005, 10, 471-482;
4. c) A. Nören-Müller, I. Reis Corrêa Jr., C. Rosenbaum, H. Schwalbe, D. Vestweber, H. Prinz, H. Schiewe, H. Waldmann, Proc. Natl. Acad. Sci. USA 2006, in press.
5. M. A. Koch, L. O. Wittenberg, S. Basu, D. A. Jeyaraj, E. Gourzoulidou, K. Reinecke, A. Odermatt, H. Waldmann, Proc. Natl. Acad. Sci. USA 2004, 101, 16721-16726.
6. M. A. Koch, A. Schuffenhauer, M. Scheck, S. Wetzel, M. Casaulta, A. Odermatt, P. Ertl, H. Waldmann, Proc. Natl. Acad. Sci. USA 2005, 102, 17272-17277.
7. For reviews, see: a) M. C. Elliott, J. Chem. Soc., Perkin Trans. 1 2002, 2301-2323;
8. b) E. Alvarez, M. L. Candenas, R. Pérez, J. L. Ravelo, J. D. Martín Chem. Rev. 1995, 95, 1953-1980;
9. c) Y. M. Shimizu Chem. Rev. 1993, 93, 1685-1698;
10. d) T. Yasumoto, M. Murata, Chem. Rev. 1993, 93, 1897-1909.
11. a) K-S. Lee, G. Li, S. H. Kim, C.-S. Lee, M.-H. Woo, S.-H. Lee, Y.-D. Jhang, J.-K. Son, J. Nat. Prod. 2002, 65, 1707-1708;
12. b) M. S. Ali, Y. Tezuka, A. H. Banskota, S. Kadota, J. Nat. Prod. 2001, 64, 491;
13. c) Y. Tezuka, A. M. S. Ali, H. Banskota, S. Kadota, Tetrahedron Lett. 2000, 41, 5903-5907;
14. d) J. K. Prasain, J. X. Li, Y. Tezuka, K. Tanaka, P. Basnet, H. Dong, T. Namba, S. Kadota, J. Nat. Prod. 1998, 61, 212-216;
15. e) Z-H. Jiang, T. Tanaka, H. Hirata, R. Fukuoka, I. Kouno, Phytochemistry 1996, 43, 1049-1053.
16. For different competitive similar approaches to tetrahydropyrans in solution, see: a) Q. Gao, T. Maruyama, M. Mouri, H. Yamamoto J. Org. Chem. 1992, 57, 1951-1952;
17. b) M. T. Mujica, M. M. Afonso, A. Galindo, J. A. Palenzuela J. Org. Chem. 1998, 63, 9728-9738;
18. c) I. Paterson, C. A. Luckhurst Tetrahedron Lett. 2003, 44, 3749-3754;
19. d) E. Ruijter, H Schültingkemper, L. A. Wessjohann J. Org. Chem. 2005, 70, 2820-2823.
20. For a review of Diels-Alder reactions on solid supports, see: J. Yil-Kauhaluoma, Tetrahedron 2001, 57, 7053-7071.
21. a) M. G. Leuenberger, T. Leßmann, M. Lopez-Canet, S. Menninger, O. Müller, S. Hümmer, J. Bormann, E. Fava, M. Zerial, T. U. Mayer, H. Waldmann, submitted;
22. for enantioselective hetero Diels-Alder reactions with inverse electron demand on the solid support, i. e., the employment of α,β-unsaturated carbonyl compounds and enol ethers see: b) G. Dujardin, S. Leconte, L. Coutable, E. Brown, Tetrahedron Lett. 2001, 42, 8849-8852;
23. c) R. A. Stavenger, S. L. Schreiber, Angew. Chem. Int. Ed. 2001, 40, 3417-3421;
24. d) M. Kurosu, J. R. Porter, M. A. Foley, Tetrahedron Lett. 2004, 45, 145-148.
25. a) J. A. López-Peligrín, K. D. Janda, Chem. Eur. J. 2000, 6, 1917-1922;
26. b) S. Hanessian, J. Ma, W. Wang, Tetrahedron Lett. 1999, 40, 4631-4634;
27. c) K. J. Lee, A. Angulo, P. Ghazal, K. D. Janda, Org. Lett. 1999, 1, 1859-1862;
28. d) C. Chen, I. A. McDonald, B. Munoz, Tetrahedron Lett. 1998, 39, 217-220;
29. e) S. Chen, K. D. Janda, J. Am. Chem. Soc. 1997, 119, 8724-8725.
30. K. Aikawa, R. Irie, T. Katsuki, Tetrahedron 2001, 57, 845-851.
31. a) G. D. Joly, E. N. Jacobsen, Org. Lett. 2002, 4, 1795-1798;
32. b) A. G. Dossetter, T. F. Jamison, E. N. Jacobsen Angew. Chem. Int. Ed. 1999, 38, 2398-2400.
33. [9].
34. B. H. Lipshutz, S. Sengupta, Organic Reactions 1992, 41, 135-631.