An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes

Journal of the American Chemical Society

Volumn 130, Issue 36, 2008, Pages 11970-11978

  Trost, Barry M ^a   Livingston, Robert C ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; COMPLEXATION; DEUTERIUM; INDIUM; LABELING; SUGAR (SUCROSE);

PROPARGYLIC ALCOHOLS; SYNTHESIS OF; TURN-OVER NUMBERS;

RUTHENIUM COMPOUNDS;

ALCOHOL DERIVATIVE; BRONSTED ACID; CAMPHORSULFONIC ACID; DEUTERIUM; INDENYLBIS(TRIPHENYLPHOSPHINE)RUTHENIUM CHLORIDE; INDIUM; INDIUM TRIFLATE; LEUKOTRIENE B4; LEUKOTRIENE DERIVATIVE; PROPARGYLIC ALCOHOL DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CATALYST; COMPLEX FORMATION; ISOMERIZATION; MOLECULAR STABILITY; OXIDATION REDUCTION REACTION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

ALKYNES; CATALYSIS; ISOMERISM; LEUKOTRIENE B4; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PROPANOLS; RUTHENIUM;

EID: 51749085800     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja804105m     Document Type: Article

References (75)

1. Swaminathan, S.; Narayanan, K. V. Chem. Rev. 1971, 71, 429.
2. For recent metal-catalyzed versions see: Bustelo, E.; Dixneuf, P. H. Adv. Synth. Catal. 2007, 349, 933.
3. Cadierno, V.; Garcia-Garrido, S. E.; Gimeno, J. Adv. Synth. Catal. 2006, 348, 101.
4. Lopez, S. S.; Engel, D. A.; Dudley, G. B. Synlett 2007, 949.
5. For recent examples, see: Sonye, J. P.; Koide, K. J. Org. Chem. 2007, 72, 1846.
6. Sonye, J. P.; Koide, K. J. Org. Chem. 2006, 71, 6254.
7. Sonye, J. P.; Koide, K. Org. Lett. 2006, 8, 199.
8. Erenler, R.; Biellmann, J. F. Tetrahedron Lett. 2005, 46, 5683.
9. Bernotas, R. C. Synlett 2004, 2165.
10. Coelho, A.; Sotelo, E.; Ravina, E. Tetrahedron 2003, 59, 2477.
11. Ishikawa, T.; Mizuta, T.; Hagiwara, K.; Aikawa, T.; Kudo, T.; Saito, S. J. Org. Chem. 2003, 68, 3702.
12. Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
13. Other examples reported as metal-catalyzed are possibly phosphine mediated: Saiah, M. K. E.; Pellicciari, R. Tetrahedron Lett. 1995, 36, 4497.
14. Guo, C.; Lu, X. J. Chem. Soc., Perkin Trans. 1 1993, 1921.
15. Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992, 428, 259.
16. Lu, X.; Ji, J.; Ma, D.; Shen, W. J. Org. Chem. 1991, 56, 5774.
17. Ma, D.; Lu, X. Tetrahedron Lett. 1989, 30, 2109.
18. Tanaka, K.; Shoji, T.; Hirano, M. Eur. J. Org. Chem. 2007, 2687.
19. Tanaka, K.; Shoji, T. Org. Lett. 2005, 7, 3561.
20. Trost, B. M.; Livingston, R. C. J. Am. Chem. Soc. 1995, 117, 9586.
21. Ma, D.; Lu, X. J. Chem. Soc., Chem. Commun. 1989, 890.
22. Trost, B. M.; Kulaweic, R. J. J. Am. Chem. Soc. 1993, 115, 2027.
23. Trost, B. M.; Kulaweic, R. J. Tetrahedron Lett. 1991, 32, 3039.
24. Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451.
25. Casey, C. P.; O'Connor, J. M. Organometallics 1985, 4, 384.
26. Bönneman, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 248.
27. Borrini, A.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Serra, G. J. Mol. Catal. 1985, 30, 181.
28. Rerek, M. E.; Basolo, F. J. Am. Chem. Soc. 1984, 106, 5908.
29. Trost, B. M.; Sharma, S.; Schmidt, T. Tetrahedron Lett. 1993, 34, 7183.
30. Trost, B. M.; Sharma, S.; Schmidt, T. J. Am. Chem. Soc. 1992, 114, 7903.
31. Pilette, D.; Moreau, S.; Le Bozec, H.; Dixneuf, P. H.; Corrigan, J.; Carty, A. J. J. Chem. Soc., Chem. Commun. 1994, 409.
32. Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526.
33. Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1994, 475, 57.
34. Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1993, 455, 247.
35. Komiya, S.; Ito, T.; Cowie, M.; Yamamoto, A.; Ibers, J. J. Am. Chem. Soc. 1976, 98, 3874.
36. Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836.
37. Trost, B. M.; Krause, L.; Portnoy, M. J. Am. Chem. Soc. 1997, 119, 11319.
38. Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686.
39. Trost, B. M.; Vidal, B.; Thommen, M. Chem. Eur. J. 1999, 5, 1055.
40. Lehmkuhl, H.; Mauermann, H.; Benn, R. Liebigs Ann. Chem. 1980, 754.
41. For some recent examples, see: Yadav, J. S.; Prathap, I.; Tadi, B. P. Tetrahedron Lett. 2006, 47, 3773.
42. Schneider, C.; Porter, N.; Brash, A. R. Chem. Res. Toxicol. 2004, 17, 937.
43. Sun, M.; Salomon, R. G. J. Am. Chem. Soc. 2004, 126, 5699.
44. Chakraborty, T. K.; Purkait, S.; Das, S. Tetrahedron 2003, 59, 9127.
45. Corey, E. J.; Marfat, A.; Goto, G.; Brion, F. J. Am. Chem. Soc. 1980, 102, 7984.
46. Corey, E. J.; Marfat, A.; Munroe, J.; Kim, K. S.; Hopkins, P. B.; Brion, F. Terahedron Lett. 1981, 22, 1077.
47. Guindon, Y.; Zamboni, R.; Lau, C. K.; Rokach, J. Tetrahedron Lett. 1982, 23, 739.
48. Zamboni, R.; Rokach, J. Tetrahedron Lett. 1982, 23, 2631.
49. Mills, L. S.; North, P. C. Tetrahedron Lett. 1983, 24, 409.
50. Nicolaou, K. C.; Zipkin, R. E.; Dolle, R. E.; Harris, B. D. J. Am. Chem. Soc. 1984, 106, 3548.
51. Han, C.-Q.; DiTullio, D.; Wang, Y.-F.; Sih, C. J. J. Org. Chem. 1986, 51, 1253.
52. Le Merrer, Y.; Gravier, C.; Languin-Micas, D.; Depezay, J. C. Tetrahedron Lett. 1986, 27, 4161.
53. Guindon, Y.; Delorme, D.; Lau, C. K.; Zamboni, R. J. Org. Chem. 1988, 53, 267.
54. Le Merrer, Y.; Gravier-Pelletier, C.; Micas-Languin, D.; Mestre, F.; Dureault, A.; Depezay, J. C. J. Org. Chem. 1989, 54, 2409.
55. Avignon-Tropis, M.; Treilhou, M.; Lebreton, J.; Pougny, J. R.; Frechard-Ortuno, I.; Huynh, C.; Linstumelle, G. Tetrahedron Lett. 1989, 30, 6335.
56. Kobayashi, Y.; Shimazaki, T.; Taguchi, H.; Sato, F. J. Org. Chem. 1990, 55, 5324.
57. Solladie, G.; Hamdouchi, C.; Ziani-Cherif, C. Tetrahedron: Asymmetry 1991, 2, 457.
58. Avignon-Tropis, M.; Treilhou, M.; Pougny, J. R.; Frechard-Oturno, I.; Linstumelle, G. Tetrahedron 1991, 47, 7279.
59. Cremin, D.; Linstumelle, G. Tetrahedron 1992, 48, 1943.
60. Kerdesky, F. A.; Schmidt, S. P.; Brooks, D. W. J. Org. Chem. 1993, 58, 3516.
61. Solladie, G.; Urbano, A.; Stone, G. B. Tetrahedron Lett. 1994, 34, 6489.
62. Rodriguez, A.; Nomen, M.; Spur, B. W.; Godfroid, J. J.; Lee, T. H. Tetrahedron 2001, 57, 25.
63. Alami, M.; Ferri, F. Tetrahedron Lett. 1996, 37, 2763. The reaction was highly exothermic when performed on 30 mmol scale.
64. Bierer, D. E.; Dener, J. M.; Dubenko, L. G.; Gerber, R. E.; Litvak, J.; Peterli, S.; Peterli-Roth, P.; Truong, T. V.; Mao, G.; Bauer, B. E. J. Med. Chem. 1995, 38, 2628.
65. Dupradeau, F.-Y.; Prandi, J.; Beau, J.-M. Tetrahedron 1995, 51, 3205.
66. Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441.
67. Zweifel, G.; Backlund, S. J.; Leung, T. J. Am. Chem. Soc. 1978, 100, 5561.
68. Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021.
69. Morris, J.; Wishka, D. G. Tetrahedron Lett. 1986, 27, 803.
70. Charoenying, P.; Davies, D. H.; McKerrecher, D.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 1913.
71. Krasovskiy, A.; Kopp, F.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 497.
72. Trost, B. M.; Lee, C. J. Am. Chem. Soc. 2001, 123, 12191.
73. Trost, B. M.; Weiss, A. H. Org. Lett. 2006, 8, 4461.
74. Takayama, H.; Koike, T.; Aimi, N.; Sakai, S. J. Org. Chem. 1992, 57, 2173.
75. Zimmerman, B.; Lerche, H.; Severin, T. Chem. Ber. 1986, 119, 2848.