Total synthesis of enantiopure pyrrhoxanthin: Alternative methods for the stereoselective preparation of 4-alkylidenebutenolides

Chemistry - A European Journal

Volumn 19, Issue 39, 2013, Pages 13065-13074

  Vaz, Belén ^a   Otero, Leticia ^a   Álvarez, Rosana ^a   Delera, Ángel R ^a  

^a UNIVERSITY OF VIGO   (Spain)

Author keywords

catalysis; marine carotenoids; polyenes; pyrrhoxanthin; total synthesis

Indexed keywords

CONFIGURATIONALLY; MARINE CAROTENOIDS; POLYENES; PYRRHOXANTHIN; SONOGASHIRA REACTIONS; STEREO-SELECTIVE; STEREOSELECTIVE PREPARATION; TOTAL SYNTHESIS;

CATALYSIS; CONDENSATION; PIGMENTS; SILVER; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

EID: 84884532615     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301873     Document Type: Article

References (58)

1. P. Jahns, A. R. Holzwarth, Biochim. Biophys. Acta Bioenerg. 2012, 1817, 182-193.
2. P. H. Lambrev, Y. Miloslavina, P. Jahns, A. R. Holzwarth, Biochim. Biophys. Acta Bioenerg. 2012, 1817, 760-769.
3. J. E. Johansen, W. A. Svec, S. Liaaen-Jensen, F. T. Haxo, Phytochemistry 1974, 13, 2261-2271.
4. A. Loeblich III, V. E. Smith, Lipids 1968, 3, 5-13.
5. G. Britton, S. Liaaen-Jensen, H. Pfander, Carotenoids. Part 1A. Isolation and Analysis, Birkhäuser, Basel, 1995.
6. G. Britton, S. Liaaen-Jensen, H. Pfander, Carotenoids Handbook, Birkhäuser, Basel, 2004.
7. J. E. Johansen, G. Borch, S. Liaaen-Jensen, Phytochemistry 1980, 19, 441-444.
8. Y. Yamano, M. Ito, J. Chem. Soc. Perkin Trans. 1 1993, 1599-1610.
9. M. Ito, Y. Yamano, S. Sumiya, A. Wada, Pure Appl. Chem. 1994, 66, 939-946.
10. J. Burghart, R. Brückner, Angew. Chem. 2008, 120, 7777-7782
11. Angew. Chem. Int. Ed. 2008, 47, 7664-7668.
12. S. Fujii, S. Y. Chang, M. D. Burke, Angew. Chem. 2011, 123, 8008-8010
13. Angew. Chem. Int. Ed. 2011, 50, 7862-7864.
14. S. J. Lee, K. C. Gray, J. S. Paek, M. D. Burke, J. Am. Chem. Soc. 2008, 130, 466-468.
15. E. M. Woerly, A. H. Cherney, E. K. Davis, M. D. Burke, J. Am. Chem. Soc. 2010, 132, 6941-6943.
16. B. Vaz, M. Domínguez, R. Álvarez, A. R. deLera, J. Org. Chem. 2006, 71, 5914-5920.
17. C. Aïssa, Eur. J. Org. Chem. 2009, 1831-1844.
18. P. R. Blakemore, J. Chem. Soc. Perkin Trans. 1 2002, 2563-2585.
19. A. Sorg, R. Brückner, Synlett 2005, 289-293.
20. B. Vaz, R. Álvarez, J. A. Souto, A. R. deLera, Synlett 2005, 294-298.
21. N. Furuichi, H. Hara, T. Osaki, H. Mori, S. Katsumura, Angew. Chem. 2002, 114, 1065-1068
22. Angew. Chem. Int. Ed. 2002, 41, 1023-1026.
23. G. Britton, S. Liaaen-Jensen, H. Pfander, Carotenoids, Vol.2. Synthesis, Birkhäuser, Basel, 1996.
24. Y. Yamano, M. V. Chary, A. Wada, Org. Biomol. Chem. 2012, 10, 4103-4108.
25. Y. Yamano, M. Ito, Org. Biomol. Chem. 2007, 5, 3207-3212.
26. T. Brodmann, D. Janssen, M. Kalesse, J. Am. Chem. Soc. 2010, 132, 13610-13611.
27. M. Acemoglu, C. H. Eugster, Helv. Chim. Acta 1984, 67, 471-487.
28. J. A. Haugan, G. Englert, T. Aakermann, E. Glinz, S. Liaaen-Jensen, Acta Chem. Scand. 1994, 48, 769-779.
29. D.-J. Dong, H.-H. Li, S.-K. Tian, J. Am. Chem. Soc. 2010, 132, 5018-5020.
30. R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874-922.
31. R. Brückner, Curr. Org. Chem. 2001, 5, 679-718.
32. F. C. Görth, R. Brückner, Synthesis 1999, 1520-1528.
33. T. Olpp, R. Brückner, Angew. Chem. 2005, 117, 1577-1581
34. Angew. Chem. Int. Ed. 2005, 44, 1553-1557.
35. A. Sorg, K. Siegel, R. Brückner, Synlett 2004, 321-325.
36. B. Vaz, R. Álvarez, R. Brückner, A. R. deLera, Org. Lett. 2005, 7, 545-548.
37. F. vonderOhe, R. Brückner, New J. Chem. 2000, 24, 659-669.
38. T. Olpp, R. Brückner, Angew. Chem. 2006, 118, 4128-4132
39. Angew. Chem. Int. Ed. 2006, 45, 4023-4027.
40. I-induced Sonogashira-lactonization of the same dihaloacrylates has been described
41. S. Inack Ngi, K. Cherry, V. Héran, L. Commeiras, J.-L. Parrain, A. Duchêne, M. Abarbri, J. Thibonnet, Chem. Eur. J. 2011, 17, 13692-13696.
42. L. Otero, B. Vaz, R. Álvarez, A. R. deLera, Chem. Commun. 2013, 49, 5043-5045.
43. W. C. Still, C. Gennari, Tetrahedron Lett. 1983, 24, 4405-4408.
44. B. H. Lipshutz, Ž. V. Boškovic̈, D. H. Aue, Angew. Chem. 2008, 120, 10337-10340
45. Angew. Chem. Int. Ed. 2008, 47, 10183-10186.
46. F. Bellina, A. Carpita, M. D. Santis, R. Rossi, Tetrahedron Lett. 1994, 35, 6913-6916.
47. B. Vaz, M. Domínguez, R. Álvarez, A. R. deLera, Chem. Eur. J. 2007, 13, 1273-1290.
48. A. Fürstner, J.-A. Funel, M. Tremblay, L. C. Bouchez, C. Nevado, M. Waser, J. Ackerstaff, C. C. Stimson, Chem. Commun. 2008, 2873-2875.
49. K. A. Scheidt, H. Chen, B. C. Follows, S. R. Chemler, D. S. Coffey, W. R. Roush, J. Org. Chem. 1998, 63, 6436-6437.
50. E. A. Ilardi, C. E. Stivala, A. Zakarian, Org. Lett. 2008, 10, 1727-1730.
51. M. Sidera, A. M. Costa, J. Vilarrasa, Org. Lett. 2011, 13, 4934-4937.
52. J. Z. Deng, D. V. Paone, A. T. Ginnetti, H. Kurihara, S. D. Dreher, S. A. Weissman, S. R. Stauffer, C. S. Burgey, Org. Lett. 2009, 11, 345-347.
53. X. Gao, D. G. Hall, J. Am. Chem. Soc. 2005, 127, 1628-1629.
54. K. C. Nicolaou, A. A. Estrada, M. Zak, S. H. Lee, B. S. Safina, Angew. Chem. 2005, 117, 1402-1406
55. Angew. Chem. Int. Ed. 2005, 44, 1378-1382.
56. N. Furuichi, H. Hara, T. Osaki, M. Nakano, H. Mori, S. Katsumura, J. Org. Chem. 2004, 69, 7949-7959.
57. A. S. Kende, K. Liu, I. Kaldor, G. Dorey, K. Koch, J. Am. Chem. Soc. 1995, 117, 8258-8270.
58. R. J. Barney, R. M. Richardson, D. F. Wiemer, J. Org. Chem. 2011, 76, 2875-2879.