Applications of olefin cross metathesis to commercial products

Advanced Synthesis and Catalysis

Volumn 344, Issue 6-7, 2002, Pages 728-735

  Pederson, Richard L ^a   Fellows, Ingrid M ^a   Ung, Thay A ^a   Ishihara, Hiroki ^a   Hajela, Sharad P ^a  

^a Materia Inc   (United States)

Author keywords

Cross metathesis; Insect pheromones; Organocatalysis; Pharmaceuticals; Ruthenium catalyst removal

Indexed keywords

EID: 0242414332     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/1615-4169(200208)344:6/7<728::AID-ADSC728>3.0.CO;2-4     Document Type: Article

References (72)

1. a) M. D. Cummings, R. W. Marquis Jr., Y. Ru, S. K. Thompson, D. F. Veber, D. S. Yamashita, (Smithkline Beecham Corp.); WO 01/70232 A1, 2001; Chem. Abstr. 2001, 135, 273219;
2. R. W. Marquis Jr., Y. Ru, D. F. Veber, M. D. Cummings D. S. Yamashita, (Smithkline Beecham Corp.), WO 00/38687, 2000; Chem. Abstr. 2000, 133, 89444;
3. Y. S. Tsantrizos, D. R. Cameron, A.-M. Faucher, E. Ghiro, N. Goudreau, M. Llinas-Brunet, (Boehringer Ingelheim Ltd.), WO 00/59929, 2000; Chem. Abstr. 2000, 133, 2966659;
4. D. A. Heerding, (Smithkline Beecham Corp.), WO 00/12515, 2000; Chem. Abstr. 2000, 132, 194368;
5. b) D. C. Harrowven, M. C. Lucas, P. D. Howes, Tetrahedron Lett. 2000, 41, 8958-8987;
6. S. Liras, M. P. Allen, J. F. Blake, Org. Lett. 2001, 3, 3483-3486;
7. C. J. Creighton, A. B. Reitz, Org. Lett. 2001, 3, 893-895;
8. D. J. Wallace, J. M. Goodman, D. J. Kennedy, A. J. Davies, C. J. Cowden, M. S. Ashwood, I. F. Cottrell, U.-H. Dolling, P. J. Reider, Org. Lett. 2001, 3, 671-674.
9. a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446;
10. b) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124;
11. Angew. Chem. Int. Ed. Engl. 1997, 36, 2067;
12. c) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371;
13. d) S. Blechert, Pure Appl. Chem. 1999, 71, 1393;
14. e) S. Kurosawa, M. Bando, K. Mori, Eur. J. Org. Chem. 2001, 4395-4399;
15. f) M. Scholl, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 1425-1428.
16. R. L. Pederson, R. H. Grubbs, (TillieChem, Inc.), U. S. Patent 6,219,019, 2001; Chem. Abstr. 2002, 136, 200046.
17. R. L. Pederson, R. H. Grubbs, (TillieChem, Inc.), WO 01/36368 A2, 2001; Chem. Abstr. 2001, 135, 5481.
18. A. Fürstner, K. Langemann, Synthesis 1997, 792-803.
19. T. L. Chio, C. H. Lee, A. K. Chatterjee, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 10417-10418;
20. A. K. Chatterjee, J. P. Morgan, M. Scholl, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 3783-3784.
21. A. Fürstner, K. Langemann, N. Kindler, (Studiengesellschaft Kohle MBH), U. S. Patent 5,936,100, 1999; Chem. Abstr. 1999, 131, 144523.
22. A. Fürstner, Angew. Chem. 2000, 112, 3140-3172;
23. Angew. Chem. Int. Ed. Engl. 2000, 39, 3012-3043.
24. a) S. D. Burke, N. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829;
25. b) S. D. Burke, E. A. Voight, Org. Lett. 2001, 3, 237-240;
26. c) M. L. Randall, J. A. Tallarico, M. L. Snapper, J. Am. Chem. Soc. 1995, 117, 9610-9611.
27. P. E. Howse, I. D. R. Stevens, O. T. Jones, Insect Pheromones and their Use in Pest Management, Chapman & Hall, New York, 1998, pp. 314-338.
28. A. Shani, CHEMTECH 1998, 28, 30-35.
29. W. L. Roelofs, Environmental Entomology 1975 4, 580.
30. R. L. Pederson, R. H. Grubbs, (Bend Research, Inc.), U. S. Patent 5,916,983, 1999; Chem. Abstr. 1999, 131, 89339.
31. J. G. Millar, R. E. Rice, J. Econ. Entomol. 1996, 89, 131-133.
32. a) M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 41, 2247;
33. b) P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110;
34. c) M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953-956;
35. d) T. E. Wilhelm, T. R. Belderrain, S. N. Brown, R. H. Grubbs, Organometallics 1997, 16, 3867.
36. 2-CH=), 5.38 (m, 2H, CH=CH).
37. 3): δ = 20.61, 25.60, 25.76, 26.53, 27.86, 27.99, 31.88, 63.95, 63.98, 129.28, 129.83, 170.29.
38. The major impurities were E,Z-4-decenyl acetate, E,Z-6-decenyl acetate, E,Z-4-nonenyl acetate, E,Z-5-nonenyl acetate, E,Z-5-undecenyl acetate and E,Z-6-undecenyl acetate. These impurities were synthesized and co-injected to verify compounds or characterized by GC-MS.
39. A. S. Hill, W. L. Roelofs, J. Chem. Ecol. 1975, 1, 91-99.
40. S. C. Stinson, Chem. Eng. News 2000, 43, 55-79.
41. N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370-4371.
42. J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172-1173.
43. W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874-9875.
44. K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244.
45. H. Pracejus, Justus Liebigs Ann. Chem. 1960, 634, 9.
46. Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615.
47. a) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396;
48. b) B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573-575;
49. c) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337.
50. a) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954;
51. b) A. Cordova, W. Notz, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842.
52. P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2001, 40, 3726-3748.
53. a) G. R. Lenz, Chemtracts-Organic Chemistry 2000, 13, 917-921;
54. b) J. J. Talley, S. R. Bertenshaw, D. L. Brown, J. S. Carter, M. J. Graneto, M. S. Kellogg, C. M. Koboldt, J. Yuan, K. Seibert, J. Med. Chem. 2000, 43, 1661.
55. a) I. R. Lynch, P.C. Buxton, J. E. Richardson, M. W. Wood-Kaezmar, R. D. Barnes, A. D. Curzons, (SmithKline Beecham pls; Ferrosan A/S), U. S. Patent 4, 721, 723, 1986; Chem. Abstr. 1987, 107, 141102;
56. b) M. N. Serradell, J. Castaner, Drugs. Fut. 1986, 2, 112.
57. S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168-8179.
58. J. S. Kingsbury, J. P. A. Harrity, P. J. Bonitatebus Jr., A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 791-799.
59. A. H. Hoveyda, R. R. Schrock, Chem. Eur. J. 2001, 7, 945-950.
60. Compound 18 was synthesized by monobenzoylation of 2-butene-1,4-diol, followed by PCC oxidation with 35-40% yield.
61. D. W. C. MacMillan, C. Countryman, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California, USA, manuscript in preparation, 2002.
62. Compound 22 was synthesized by Wittig coupling with p-fluorobenzaldehyde to yield ethyl p-fluorocinnamate. Reduction with DiBAl resulted in mainly p-fluorocinnamyl alcohol. Swern oxidation of the alcohol resulted in a complex mixture, which was difficult to purify by silica gel chromatography.
63. a) S. Gessler, S. Randl, S. Blechert, Tetrahedron Lett. 2000, 41, 9973-9976;
64. b) S. Randl, S. Gessler, H. Wakamatsu, S. Blechert, Synlett 2001, 3, 430-432;
65. c) J. Cossy, S. BouzBouz, A. Hoveyda J. Organomet. Chem. 2001, 624, 327-332;
66. d) S. Imhof, S. Randl, S. Blechert, Chem. Commun. 2001, 1692-1693;
67. e) S. Randl, S. Connon, S. Blechert, Chem. Commun. 2001, 1796-1797.
68. GC analysis with FID detector and J&W DB-225™ column 30 m × 0.25 mm (ID) × 0.25 μm film thickness. GC conditions: Initial temperature 40 °C, hold 1 minute; first ramp rate 8 °C/minute to 140 °C, hold 5 minutes; second ramp 20 °C/minute to 210 °C hold 5 minutes. 7 (E- and Z-isomers) Rt 5.76 min and 5.86 min; 8 (E- and Z-isomers) Rt 27.31 min and 27.36 min; and 9 (E-isomer) Rt 17.62 min, 9 (Z-isomer) Rt 17.74 min.
69. H. Maynard; R. H. Grubbs, Tetrahedron Lett. 1999, 40, 4137-4140.
70. This set-up allows 10 to be removed with < 10% loss of 11.
71. GC analysis with FID detector and J&W DB-5TM column 30 m × 0.25 mm (ID) × 0.25 μm film thickness. GC conditions: Initial temperature 100 °C, hold 0 minute; ramp rate 25 °C/minute to 240 °C, hold 10 minutes. Oleyl alcohol Rt 6.103 min; 11-eicosenol Rt 6.920 min; 13-docosenol 8.007 min; oleyl acetate Rt 6.548 min; 13 Rt 7.499 min; 13-docosenyl acetate 8.249 min.
72. GC analysis with FID detector and J&W DB-225™ column 30 m × 0.25 mm (ID) × 0.25 μm film thickness. GC conditions: Initial temperature 100 °C, hold 0 minute; ramp rate 25 °C/minute to 200 °C, hold 15 minutes. 11 (E-isomer) Rt 8.24 min and 11 (Z-isomer) Rt 8.38 min.