Stereoselective total synthesis of serine palmitoyl-CoA transferase inhibitors

Synthesis

Volumn , Issue 15, 2006, Pages 2447-2474

  Byun, Hoe Sup ^a   Lu, Xuequan ^a   Bittman, Robert ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

Antifungal agents; Inhibitors; Natural products; Sphingolipids; Stereoselective synthesis

Indexed keywords

BIOSYNTHESIS; ENZYMES; FUNGI; LIPIDS; METABOLITES;

ANTIFUNGAL AGENTS; INHIBITORS; NATURAL PRODUCTS; SPHINGOLIPIDS; STEREOSELECTIVE SYNTHESIS;

ENZYME INHIBITION;

ALKENYLIODIDE DERIVATIVE; ALLYL ALCOHOL; CARBOHYDRATE DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; IODINE DERIVATIVE; MYCESTERICIN; OXAZOLIDINE DERIVATIVE; PALLADIUM; SERINE PALMITOYL COA TRANSFERASE INHIBITOR; SERINE PALMITOYLTRANSFERASE; SPHINGOFUNGIN; SPHINGOFUNGIN B; SPHINGOLIPID; SULFAMISTERIN; THERMOZYMOCIDIN; THREITOL; TRANSFERASE INHIBITOR; UNCLASSIFIED DRUG; VIRIDIOFUNGIN;

ACYLATION; ALDOL REACTION; ANIMAL CELL; BAYLIS HILLMAN REACTION; BIOLOGICAL ACTIVITY; CATALYSIS; CHEMICAL BOND; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME INHIBITION; EPIMER; FUNGUS; LIPOGENESIS; METABOLITE; MOUSE; NONHUMAN; OLEFINATION; REVIEW; STEREOCHEMISTRY; WITTIG REACTION;

EID: 33747172279     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942475     Document Type: Review

References (85)

1. Merrill, A. H. Jr.; Sandhoff, K. In Biochemistry of Lipids, Lipoproteins, and Membranes, 4th ed.; Vance, D. E.; Vance, J. E., Eds.; Elsevier: Amsterdam, 2002, 373-407.
2. Cowart, L. A.; Hannun, Y. A. Biochem. Soc. Trans. 2005, 33, 1166.
3. Hanada, K. Biochim. Biophys. Acta 2003, 1632, 16.
4. Hanada, K.; Nishijima, M.; Fujita, T.; Kobayashi, S. Biochem. Pharmacol. 2000, 59, 1211.
5. Riley, R. T.; Plattner, R. D. Methods Enzymol. 2000, 311, 348.
6. Mandala, S.; Harris, G. H. Methods Enzymol. 2000, 311, 335.
7. Miyaka, T.; Kozutsumi, Y.; Nakamura, S.; Fujita, T.; Kawasaki, T. Biochem. Biophys. Res. Commun. 1995, 211, 396.
8. Fujita, T.; Hirose, M.; Yoneta, M.; Sasaki, S.; Inoue, K.; Kiuchi, M.; Hirase, S.; Chiba, K.; Sakamoto, H.; Arita, M. J. Med. Chem. 1996, 39, 4451.
9. Payette, D. R.; Just, G. Can. J. Chem. 1981, 59, 269.
10. Al Neirabeyeh, M.; Ziegler, J. C.; Gross, B.; Caubère, P. Synthesis 1976, 811.
11. Sano, S.; Kobayashi, Y.; Kondo, T.; Takebayashi, M.; Maruyama, S.; Fujita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097.
12. Liu, D.-G.; Wang, B.; Lin, G.-Q. J. Org. Chem. 2000, 65, 9114.
13. Oishi, T.; Ando, K.; Inomiya, K.; Sato, H.; Iida, M.; Chida, N. Bull. Chem. Soc. Jpn. 2002, 75, 1927.
14. Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S. Chem. Commun. 2001, 2030.
15. Trost, B. M.; Lee, C. J. Am. Chem. Soc. 2001, 123, 12191.
16. Lee, K.-Y.; Oh, C.-Y.; Kim, Y.-H.; Joo, J.-E.; Ham, W.-H. Tetrahedron Lett. 2002, 43, 9361.
17. Pollex, A.; Millet, A.; Müller, J.; Hiersemann, M.; Abraham, L. J. Org. Chem. 2005, 70, 5579.
18. Sato, H.; Maeba, T.; Yanase, R.; Yamaji-Hasegawa, A.; Kobayashi, T.; Chida, N. J. Antibiot. 2005, 58, 37.
19. Otaka, K.; Mori, K. Eur. J. Org. Chem. 1999, 1795.
20. Abrams, S. R. Can. J. Chem. 1984, 62, 1333.
21. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908.
22. Kobayashi, S.; Furuta, T. Tetrahedron 1998, 54, 10275.
23. Mukaiyama, T.; Kobayashi, S. Org. React. 1994, 46, 1-103.
24. Lee, K.-Y.; Oh, C.-Y.; Ham, W.-H. Org. Lett. 2002, 4, 4403.
25. Banfi, L.; Beretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1983, 1613.
26. Rao, A. V. R.; Gurja, M. K.; Devi, T. R.; Kumar, K. R. Tetrahedron Lett. 1993, 34, 1653.
27. Hughes, D. L. Org. React. 1992, 42, 335-656.
28. Deloisy, S.; Thang, T. T.; Olesker, A.; Lukacs, G. Tetrahedron Lett. 1994, 35, 4783.
29. Pravdic, N.; Fletcher, H. G. Jr. Carbohvdr. Res. 1971, 19, 339.
30. Wollenberg, R. H.; Miller, S. J. Tetrahedron Lett. 1978, 19, 3219.
31. McMurry, J. E.; Melton, J.; Padgett, H. J. Org. Chem. 1974, 39, 259.
32. Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N. Tetrahedron 1995, 51, 6209.
33. Overman, L. E.; Carpenter, N. E. Org. React. 2005, 66, 1-108.
34. Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285.
35. Dax, K.; Glänzer, B. I.; Schulz, G.; Vyplel, H. Carbohydr. Res. 1987, 162, 13.
36. Fürstner, A.; Weidmann, H. J. Carbohydr. Chem. 1988, 7, 773.
37. Nishikawa, T.; Asai, M.; Ohyabu, N.; Isobe, M. J. Org. Chem. 1998, 63, 188.
38. Nakamura, T.; Shiozaki, M. Tetrahedron 2002, 58, 8779.
39. Haines, I. M.; Singleton, E. J. Chem. Soc., Dalton Trans. 1972, 1891.
40. Oltvoon, J. J.; van Boeckel, C. A. A.; de Konig, J. H.; van Boom, J. H. Synthesis 1981, 305.
41. Mash, E. A.; Nelson, K. A.; Densen, S. V.; Hemperly, S. B. Org. Synth. 1990, 68, 92-103.
42. Wang, B.; Yu, X.-M.; Lin, G.-Q. Synlett 2001, 904.
43. Schmidt, U.; Respondek, M.; Lieberknecht, A.; Werner, J.; Fischer, P. Synthesis 1989, 256.
44. Rossiter, B. E.; Verhoeven, T. R.; Sharpless, K. B. Tetrahedron Lett. 1979, 20, 4733.
45. Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada, H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887.
46. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 2001, 123, 3687.
47. Fleming, I.; Sanderson, P. E. J. Tetrahedron Lett. 1987, 28, 4229.
48. Esumi, T.; Iwabuchi, Y.; Irie, H.; Hatakeyama, S. Tetrahedron Lett. 1998, 39, 877.
49. Morokuma, K.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Chem. Commun. 2005, 2265.
50. Shibata, K.; Shingu, K.; Vassilev, V. P.; Nishide, K.; Fujita, T.; Node, M.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 2791.
51. Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031.
52. Banfi, L.; Beretta, M. G.; Colombo, L.; Gennari, C.; Scolastico, C. J. Chem. Soc., Chem. Commun. 1982, 488.
53. Mori, K.; Otaka, K. Tetrahedron Lett. 1994, 35, 9207.
54. Takai, K.; Takashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048.
55. Jin, H.; Uenish, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644.
56. Fujita, T.; Hamamichi, N.; Matusuzaki, T.; Kitao, Y.; Kiuchi, M.; Node, M.; Hirose, R. Tetrahedron Lett. 1995, 36, 8599.
57. Just, G.; Payette, D. R. Tetrahedron Lett. 1980, 21, 3219.
58. Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822.
59. Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Murakami, N Chem. Pharm. Bull. 1994, 42, 994.
60. Hatakeyama, S.; Matsumoto, H.; Fukuyama, H.; Mukugi, Y.; Irie, H. J. Org. Chem. 1997, 62, 2275.
61. Oishi, T.; Ando, K.; Chida, N. Chem. Commun. 2001, 1932.
62. Oishi, T.; Ando, K.; Inomiya, K.; Sato, H.; Iida, M.; Chida, N. Org. Lett. 2002, 4, 151.
63. Pollex, A.; Abraham, L.; Müller, J.; Hiersemann, M. Tetrahedron Lett. 2004, 45, 6915.
64. Schlosser, M. Top. Stereochem. 1970, 5, 1.
65. Schöllkopf, U. Pure Appl. Chem. 1983, 55, 1799.
66. Kobayashi, S.; Hayashi, T.; Iwamoto, S.; Furuta, T.; Matsumura, M. Synlett 1996, 627.
67. Kobayashi, S.; Matsumura, M.; Furuta, T.; Hayashi, T.; Iwamoto, S. Synlett 1997, 301.
68. Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219.
69. Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B. III J. Am. Chem. Soc. 1996, 118, 3584.
70. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1988, 120, 6818.
71. Takai, T.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
72. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
73. Nakamura, T.; Shiozaki, M. Tetrahedron Lett. 2001, 42, 2701.
74. Williams, D. R.; Kissel, W. S. J. Am. Chem. Soc. 1998, 120, 11198.
75. Negishi, E.; Ay, M.; Gulevich, Y. V.; Noda, Y. Tetrahedron Lett. 1993, 34, 1437.
76. Zweerink, M. M.; Edison, A. M.; Wells, G. B.; Pinto, W.; Lester, R. C. J. Biol. Chem. 1992, 267, 25032.
77. Yamaji-Hasegawa, A.; Takahashi, A.; Tetsuka, Y.; Senoh, Y.; Kobayashi, T. Biochemistry 2005, 44, 268.
78. Mandala, S. M.; Thornton, R. A.; Frommer, B. R.; Dreikorn, S.; Kurtz, M. B. J. Antibiot. 1997, 50, 339.
79. Sasaki, S.; Hashimoto, R.; Kiuchi, M.; Inoue, K.; Ikumoto, T.; Hirose, R.; Chiba, K.; Hoshino, Y.; Okumoto, T.; Fujita, T. J. Antibiot. 1994, 47, 420.
80. Fujita, T.; Hamamichi, N.; Kiuchi, M.; Matsuzaki, T.; Kitao, Y.; Inoue, K.; Hirose, R.; Yonata, M.; Sasaki, S.; Chiba, K. J. Antibiot. 1996, 49, 846.
81. Yoshikawa, M.; Yokokawa, Y.; Okuno, Y.; Yagi, N.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 2662.
82. Ikushiro, H.; Hayashi, H.; Kagamiyama, H. Biochemistry 2004, 43, 1082.
83. Brunner, M.; Koskinen, A. M. P. Curr. Org. Chem. 2004, 8, 1629.
84. Liao, J.; Tao, J.; Lin, G.; Liu, D. Tetrahedron 2005, 61, 4715.
85. Kang, S. H.; Kang, S. Y.; Lee, H.-S.; Buglass, A. J. Chem. Rev. 2005, 105, 4537.