Total synthesis of naturally configured pyrrhoxanthin, a carotenoid butenolide from plankton

Angewandte Chemie - International Edition

Volumn 47, Issue 40, 2008, Pages 7664-7668

  Burghart, Johen ^a   Brückner, Reinhard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Bifunctional building blocks; Cross coupling; Dyes pigments; Natural products; Total syntheses

Indexed keywords

SYNTHESIS (CHEMICAL);

BIFUNCTIONAL BUILDING BLOCKS; CROSS-COUPLING; DYES/PIGMENTS; NATURAL PRODUCTS; TOTAL SYNTHESES;

COMPLEXATION;

BIOLOGICAL PRODUCT; CAROTENOID; DRUG DERIVATIVE; GAMMA BUTYROLACTONE; PYRRHOXANTHIN;

ARTICLE; CHEMISTRY; PLANKTON; SYNTHESIS;

4-BUTYROLACTONE; BIOLOGICAL PRODUCTS; CAROTENOIDS; PLANKTON;

EID: 54749100736     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801638     Document Type: Article

References (91)

1. a) W. A. Svec, S. Liaaen-Jensen, F. T. Haxo, Phytochemistry 1974, 13, 2261-2271;
2. b) T. Aakermann, S. Liaaen-Jensen, Phytochemistry 1992, 31, 1779-1782.
3. Carotenoids-Handbook (Eds.: G. Britton, S. Liaaen-Jensen, H. Pfander), Birkhäuser, Basel, 2004.
4. a) A. R. Loeblich III, V. E. Smith, Lipids 1968, 3, 5-13;
5. b) Ref. [1a];
6. c) T. Skjenstad, F. T. Haxo, S. Liaaen-Jensen, Biochem. Syst. Ecol. 1984, 12, 149-153;
7. d) T. Bjørnland, Biochem. Syst. Ecol. 1990, 18, 307-316;
8. e) Ref. [1b].
9. a) H. H. Strain, W. A. Svec, P. Wegfahrt, H. Rapoport, F. T. Haxo, S. Norgård, H. Kjøsen, S. Liaaen-Jensen, Acta Chem. Scand. Ser. B 1976, 30, 109-120;
10. b) J. E. Johansen, G. Borch, S. Liaaen-Jensen, Phytochemistry 1980, 19, 441-444.
11. E. Hofmann, P. M. Wrench, F. P. Sharples, R. G. Hiller, W. Welte, K. Diederichs, Science 1996, 272, 1788-1791.
12. a) Ref. [8a];
13. b) Ref. [8b];
14. c) N. Furuichi, H. Hara, T. Osaki, H. Mori, S. Katsumura, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 2001, 43, 211-216
15. [Chem. Abs. 2002, 140, 199480];
16. d) N. Furuichi, H. Hara, T. Osaki, H. Mori, S. Katsumura, Angew. Chem. 2002, 114, 1065-1068;
17. Angew. Chem. Int. Ed. 2002, 41, 1023-1026;
18. e) N. Furuichi, H. Hara, T. Osaki, M. Nakano, H. Mori, S. Katsumura, J. Org. Chem. 2004, 69, 7949-7959;
19. f) T. Olpp, R. Brückner Angew. Chem. 2006, 118, 4128-4132;
20. Angew. Chem. Int. Ed. 2006, 45, 4023-4027;
21. Angew. Chem. Int. Ed. 2006, 45, 4023-4027;
22. g) B. Vaz, M. Domínguez, R. Álvarez, A. R. de Lera, Chem. Eur. J. 2007, 13, 1273-1290.
23. B. Vaz, M. Domínguez, R. Álvarez, A. R. de Lera, J. Org. Chem. 2006, 71, 5914-5920.
24. a) M. Ito, Y. Hirata, Y. Shibata, K. Tsukida, J. Chem. Soc. Perkin Trans. 1 1990, 197-199;
25. b) Y. Yamano, M. Ito, J. Chem. Soc. Perkin Trans. 1 1993, 1599-1610.
26. F. von der Ohe, Dissertation, Universität Freiburg, 2001, pp. 50-52, 100-103.
27. F. von der Ohe, Dissertation, Universität Freiburg, 2001, pp. 76-78.
28. Cf. the isomerization of peridinin: a) Ref. [6d];
29. b) Ref. [6f];
30. c) J. A. Haugan, G. Englert, T. Aakermann, E. Glinz, S. Liaaen-Jensen, Acta Chem. Scand. 1994, 48, 769-779;
31. d) T. Olpp, Dissertation, Universität Freiburg, 2005, pp. 204-208;
32. e) Ref. [6g].
33. H. Dinger, Dissertation, UniversitCt Freiburg, 2003, pp. 71-73, 171.
34. Reviews: a) J. K. Stille, Angew. Chem. 1986, 98, 504-519;
35. Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524;
36. b) V. Farina, G. P. Roth in Advances in Metal-Organic Chemistry, Vol. 5 (Ed.: L. S. Liebeskind), JAI Press, Greenwich, Connecticut, 1996, pp. 1-53;
37. c) V. Farina, V. Krishnamurthy, W. J. Scott, Org. React. 1997, 50, 1-652;
38. d) P. Espinet, A. M. Echavarren, Angew. Chem. 2004, 116, 4808-4839;
39. Angew. Chem. Int. Ed. 2004, 43, 4704-4734;
40. e) T. N. Mitchell in Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2. ed., Wiley-VCH, Weinheim, 2004, pp. 125-162;
41. f) M. V. N. De Souza, Curr. Org. Synth. 2006, 3, 313-326.
42. Both the bromoiodobutenolide 8 and its precursor rac-19 undergo Stille coupling first at the iodolefin moiety and then at the bromoolefin moiety as shown in Refs. [6g, 10, 15] and Ref. [16], respectively. This order of assembly is opposite to that in the synthesis reported here.
43. B. Vaz, R. Álvarez, R. Brückner, A. R. de Lera, Org. Lett. 2005, 7, 545-548.
44. F. von der Ohe, Dissertation, Universität Freiburg, 2001, pp. 82-83.
45. T. Olpp, R. Brückner, Angew. Chem. 2005, 117, 1577-1581;
46. Angew. Chem. Int. Ed. 2005, 44, 1553-1557.
47. To the best of our knowledge, the iodine analogue of bromoalkyne acetate 10 was first described in Ref. [25] (pp. 268-269).
48. J. Burghart, R. Brückner, unpublished results.
49. Reviews: a) L. A. Paquette, Org. React. 1977, 25, 1-71;
50. b) R. J. K. Taylor, G. Casy, Org. React. 2003, 62, 357-475;
51. c) X.-L. Wang, X.-P. Cao, Z.-L. Zhou, Chin. J. Org. Chem. 2003, 23, 120-128.
52. a) A. Sorg, R. BrRckner, Angew. Chem. 2004, 116, 4623-4626;
53. Angew. Chem. Int. Ed. 2004, 43, 4523-4526;
54. b) R. Brückner, K. Siegel, A. Sorg in Strategies and Tactics in Organic Synthesis, Vol. 5 (Ed.: M. Harmata), Elsevier, Amsterdam, 2004, pp. 437-473;
55. c) A. Sorg, K. Siegel, R. Brückner, Chem. Eur. J. 2005, 11, 1610-1624.
56. Vinylogous Mukaiyama aldol additions of other siloxyfuranes to iodomethacrolein also exhibit syn selectivity: a) F. von der Ohe, R. Brückner, Tetrahedron Lett. 1998, 39, 1909-1910;
57. b) F. von der Ohe, R. Brückner, New J. Chem. 2000, 24, 659-669;
58. c) Mechanistic analysis: C. S. López, R. Álvarez, B. Vaz, O. N. Faza, A. R. de Lera, J. Org. Chem. 2005, 70, 3654-3659.
59. a) R. Marini-Bettolo, C. S. J. Tsai, T. Y. R. Tsai, K. Wiesner, Heterocycles 1981, 15, 305-308;
60. b) F. von der Ohe, Dissertation, Universität Freiburg, 2001, pp. 51, 101;
61. c) H. Dinger, Dissertation, UniversitCt Freiburg, 2003, pp. 64-65, 159;
62. d) Ref. [22c];
63. e) Ref. [6g].
64. a) C. Tode, Y. Yamano, M. Ito, J. Chem. Soc. Perkin Trans. 1 1999, 1625-1626;
65. b) C. Tode, Y. Yamano, M. Ito, J. Chem. Soc. Perkin Trans. 1 2001, 3338-3345.
66. J. Schmidt-Leithoff, Dissertation, Universität Freiburg, 2006, pp. 114-116, 263-268.
67. M. Soukup, E. Widmer, T. Lukáè, Helv. Chim. Acta 1990, 73, 868-873.
68. a) Method: H. Hofmeister, K. Annen, H. Laurent, R. Wiechert, Angew. Chem. 1984, 96, 720-724;
69. Angew. Chem. Int. Ed. Engl. 1984, 23, 727-729;
70. b) in analogy to a procedure by T. V. Bohner, R. Beaudegnies, A. Vasella, Helv. Chim. Acta 1999, 82, 143-160.
71. B. H. Lipshutz, E. L. Ellsworth, S. H. Dimock, D. C. Reuter, Tetrahedron Lett. 1989, 30, 2065-2068.
72. J. Schmidt-Leithoff, R. Brückner, Helv. Chim. Acta 2005, 88, 1943-1959.
73. J. Thibonnet, V. Launay, M. Abarbri, A. Duchêne, J.-L. Parrain, Tetrahedron Lett. 1998, 39, 4277-4280.
74. J.-F. Betzer, F. Delaloge, B. Muller, A. Pancrazi, J. Prunet, J. Org. Chem. 1997, 62, 7768-7780;
75. F. C. Görth, Dissertation, Universität Freiburg, 2000, p. 125.
76. A. S.-Y. Lee, C.-W. Wu, Tetrahedron 1999, 55, 12531-12542.
77. a) Method: Ref. [34];
78. b) X.-P. Xao, Tetrahedron 2002, 58, 1301-1307;
79. c) Q. Yao, Org. Lett. 2002, 4, 427-430.
80. X.-P. Cao, T.-L. Chan, H.-F. Chow, J. Tu, J. Chem. Soc. Chem. Commun. 1995, 1297-1299.
81. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923-2925.
82. F. Texier, J. Bourgois, Bull. Soc. Chim. Fr. 1976, 487-492.
83. a) I. Hanisch, Dissertation, Universität Freiburg, 2001, pp. 62-63, 159;
84. b) Y. Murakami, M. Nakano, T. Shimofusa, N. Furuichi, S. Katsumura, Org. Biomol. Chem. 2005, 3, 1372-1374.
85. a) I. Hanisch, Dissertation, Universität Freiburg, 2001, pp. 62-63, 161;
86. b) H. Dinger, Dissertation, Universität Freiburg, 2003, p. 170;
87. c) Ref. [37b].
88. a) Footnote 9 in J. P. Marino, J. K. Long, J. Am. Chem. Soc. 1988, 110, 7916-7917;
89. b) L. S. Liebeskind, R. W. Fengl, J. Org. Chem. 1990, 55, 5359-5364.
90. Footnote 30 in J. Srogl, G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1997, 119, 12376-12377.
91. 3: G. Englert, T. Aakermann, S. Liaaen-Jensen, Magn. Reson. Chem. 1993, 31, 910-915.