Strategies for the synthesis of the cyclopropyl-substituted lactone family of oxylipins

Synlett

Volumn , Issue 11, 2009, Pages 1713-1729

  White, James D ^a   Yang, Jongtae ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

Biomimetic synthesis; Cascade synthesis; Claisen rearrangement; Cyclopropanation; Lactones; Lipids

Indexed keywords

ACETAL; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; HALICHOLACTONE; KETENE DERIVATIVE; LACTONE; LACTONE DERIVATIVE; OXYLIPIN; UNCLASSIFIED DRUG;

BIOMIMETICS; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; CYCLIZATION; REVIEW; SIMMONS SMITH REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 67649961476     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217352     Document Type: Review

References (74)

1. (a) Gerwick, W. H.; Nagle, D. G.; Proteau, P. J. Top. Curr. Chem. 1993, 167, 117.
2. (b) Gerwick, W. H. Chem. Rev. 1993, 93, 1807.
3. Gerwick, W. H.; Moghaddam, M. F.; Hamberg, M. Arch. Biochem. Biophys. 1991, 290, 436.
4. Gerwick, W. H.; Singh, I. P. In Lipid Biotechnology; Kuo, T. M.; Gardner, H. W., Eds.; Marcel Dekker: New York, 2002, 249-275.
5. (a) Niwa, H.; Wakamatsu, K.; Yamada, K. Tetrahedron Lett. 1989, 30, 4543.
6. (b) Kigoshi, H.; Niwa, H.; Yamada, K.; Stout, T. J.; Clardy, J. Tetrahedron Lett. 1991, 32, 2427.
7. Higgs, M. D.; Mulheirn, L. J. Tetrahedron 1981, 37, 4259.
8. Corey, E. J.; De, B.; Ponder, J. W.; Berg, J. M. Tetrahedron Lett. 1984, 25, 1015.
9. Corey, E. J.; Matsuda, S. P. T. Tetrahedron Lett. 1987, 28, 4247.
10. Corey, E. J.; d'Alarcoa, M.; Matsuda, S. P. T.; Lansbury, P. T. Jr.; Yamada, Y. J. Am. Chem. Soc. 1987, 109, 289.
11. Brash, A. R. J. Am. Chem. Soc. 1989, 111, 1891.
12. Baertschi, S. W.; Brash, A.; Harris, T. M. J. Am. Chem. Soc. 1989, 111, 5003.
13. White, J. D.; Jensen, M. S. J. Am. Chem. Soc. 1993, 115, 2970.
14. Jin, H.; Uenishi, J.; Christ, W.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644.
15. Gao, Y.; Hanson, R.; Klunder, J.; Ko, S. Y.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
16. Takai, K.; Nitta, K.; Utimoto, K.; Masamune, H. J. Am. Chem. Soc. 1986, 108, 7408.
17. Leusink, A. J.; Budding, H. A.; Drenth, W. J. Organomet. Chem. 1968, 11, 541.
18. Echavarren, A. M.; Tueting, D. R.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 4039.
19. Van Tamelen, E. E.; Anderson, R. J. J. Am. Chem. Soc. 1972, 94, 8225.
20. Derome, A. E. Modern NMR Techniques for Chemistry Research; Pergamon: Oxford UK, 1987, 209-220.
21. Ueno, Y.; Okawara, M. Tetrahedron Lett. 1976, 4597.
22. Nagle, D. G.; Gerwick, W. H. Tetrahedron Lett. 1990, 31, 2995.
23. Nagle, D. G.; Gerwick, W. H. J. Org. Chem. 1994, 59, 7227.
24. White, J. D.; Jensen, M. S. J. Am. Chem. Soc. 1995, 117, 6224.
25. Leblanc, Y.; Fitzsimmons, B. J.; Adams, J.; Perez, F.; Rokach, J. J. Org. Chem. 1986, 51, 789.
26. Wong, M. Y. H.; Gray, G. R. J. Am. Chem. Soc. 1978, 100, 3548.
27. Barloy-Da Silva, C.; Benkouider, A.; Pale, P. Tetrahedron Lett. 2000, 41, 3077.
28. Yu, J.; Lai, J.-Y.; Ye, J.; Balu, N.; Reddy, L. M.; Duan, W.; Fogel, E. R.; Capdevila, J. H.; Falck, J. R. Tetrahedron Lett. 2002, 43, 3939.
29. Pietruszka, J.; Wilhelm, T. Synlett 2003, 1698.
30. On constanolactones C and D, see: Pietruszka, J.; Rieche, A. C. M.; Schöne, N. Synlett 2007, 2525.
31. On constanolactone E, see: (a) Miyaoka, H.; Shigemoto, T.; Yamada, Y. Tetrahedron Lett. 1996, 37, 7407.
32. (b) Miyaoka, H.; Shigemoto, T.; Yamada, Y. Heterocycles 1998, 47, 415.
33. A proposed revision to the absolute configuration of neohalicholactone(54) was found to be in error: Proteau, P. J.; Rossi, J. V.; Gerwick, W. H. J. Nat. Prod. 1994, 57, 1717.
34. White, J. D.; Jensen, M. S. Synlett 1996, 31.
35. Fallis, A. G.; Hearn, M. T. W.; Jones, E. R. H.; Thaller, V.; Turner, J. L. J. Chem. Soc., Perkin Trans. 1 1973, 743.
36. Gannett, P. M.; Nagel, D. L.; Reilley, P. J.; Lawson, T.; Sharpe, J.; Toth, B. J. Org. Chem. 1988, 53, 1064.
37. Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshiwa, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585.
38. Martin, G. E.; Crouch, R. C. J. Nat. Prod. 1991, 54, 1.
39. Critcher, D. J.; Connolly, S.; Mahon, M. F.; Wills, M. J. Chem. Soc., Chem. Commun. 1995, 139.
40. Critcher, D. J.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763.
41. Critcher, D. J.; Connolly, S.; Wills, M. J. Org. Chem. 1997, 62, 6638.
42. (a) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tamaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653.
43. (b) Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T.; Ohishi, H.; Takemoto, Y. J. Org. Chem. 2001, 66, 81.
44. Takahashi, T.; Watanabe, H.; Kitahara, T. Heterocycles 2002, 58, 99.
45. Seo, Y.; Cho, K. W.; Rho, J.-R.; Shin, J.; Kwon, B.-M.; Bok, S.-H.; Song, J.-I. Tetrahedron 1996, 52, 10583.
46. White, J. D.; Martin, W. H. C.; Lincoln, C. M.; Yang, J. Org. Lett. 2007, 9, 3481.
47. White, J. D.; Lincoln, C. M.; Yang, J.; Martin, W. H. C.; Chan, D. B. J. Org. Chem. 2008, 73, 4139.
48. Mohapatra, D.; Yellol, G. Arkivoc 2003, (ix), 21.
49. Lincoln, C. M.; White, J. D.; Yokochi, A. F. T. Chem. Commun. 2004, 2846.
50. Tamborski, C. M.; Ford, F. E.; Soloski, E. J. J. Org. Chem. 1963, 28, 237.
51. See: (a) Nagasawa, T.; Handa, Y.; Onoguchi, Y.; Obba, S.; Suzuki, K. Synlett 1995, 739.
52. (b) Nagasawa, T.; Handa, Y.; Onoguchi, Y.; Suzuki, K. Bull. Chem. Soc. Jpn. 1996, 69, 31.
53. (c) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964; and references cited therein.
54. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
55. (a) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253.
56. (b) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883.
57. (c) Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Am. Chem. Soc. 2001, 66, 894.
58. Oshima, K.; Takai, K.; Hotta, Y.; Nozaki, H. Tetrahedron Lett. 1978, 2417.
59. -1
60. Charette, A. B.; Lebel, H. J. J. Org. Chem. 1995, 60, 2966.
61. (a) Petrzilka, M. Helv. Chim. Acta 1978, 61, 3075.
62. (b) Baudat, R.; Petrzilka, M. Helv. Chim. Acta 1979, 62, 1406.
63. (a) Robinson, R. A.; Clark, J. S.; Holmes, A. B. J. Am. Chem. Soc. 1993, 115, 10400.
64. (b) Burton, J. W.; Clark, J. S.; Derrer, S.; Stork, T. C.; Bendall, J. G.; Holmes, A. B. J. Am. Chem. Soc. 1997, 119, 7483.
65. Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. J. Org. Chem. 1986, 51, 2391.
66. Vlieghe, P.; Clerc, T.; Pannecouque, C.; Witvrouw, M.; De Clerq, E.; Salles, J. P.; Kraus, J. L. J. Med. Chem. 2001, 44, 3014.
67. Carling, R. W.; Holmes, A. B. J. Chem. Soc., Chem. Commun. 1986, 325.
68. Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392.
69. Anderson, E. A.; Davidson, J. E. P.; Harrison, J. R.; O'Sullivan, P. T.; Burton, J. W.; Collins, I.; Holmes, A. B. Tetrahedron 2002, 58, 1943.
70. Saito, S.; Hasegawa, T.; Inaba, M.; Nishida, R.; Fujii, T.; Nomizu, S.; Moriwake, T. Chem. Lett. 1984, 1389.
71. Bessodes, M.; Komiotis, D.; Autonakis, K. Tetrahedron Lett. 1986, 27, 579.
72. (a) Davoren, J. E.; Martin, S. F. J. Am. Chem. Soc. 2007, 129, 510.
73. (b) Davoren, J. E.; Harcken, C.; Martin, S. F. J. Org. Chem. 2008, 73, 391.
74. Pietruszka, J.; Rieche, A. C. M. Adv. Synth. Catal. 2008, 350, 1407.