Highly Stereocontrolled Total Synthesis of Leukotriene B4, 20-Hydroxyleukotriene B4, Leukotriene B3, and Their Analogues

Journal of Organic Chemistry

Volumn 55, Issue 19, 1990, Pages 5324-5335

  Kobayashi, Yuichi ^a   Shimazaki, Toshiyuki ^a   Taguchi, Hideki ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LEUKOTRIENE B3; LEUKOTRIENE B4; LEUKOTRIENE B4 DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; METHODOLOGY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

EID: 0025102526     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00306a007     Document Type: Article

References (50)

1. For general reviews, see: (a) Chakrin, L. W.; Bailey, D. M., Eds. The Leukotrienes, Chemistry and Biology; Academic Press: New York, 1984.
2. Samuelsson, B. Science 1983. 220. 568.
3. Ford-Hutchinson, A. W.; Bray, M. A.; Doig, M. V.; Shipley, M. E.; Smith, M. J. H. Nature (London) 1980, 286, 264.
4. Borgeat, P.; Sirois, P. J. Med. Chem. 1981, 24. 121.
5. Hansson, G.; Lindgren, J. A.; Dahlen, S.-E.; Hedqvist, P.; Samuelsson, B. FEBS Lett. 1981, 130, 107.
6. Jakschik, B. A.; Morrison, A. R.; Sprecher, H. J. Biol. Chem. 1983, 258, 12797.
7. Stenson, W. F.; Prescott, S. M.; Sprecher, H. Biol. Chem. 1984, 259, 11784.
8. Evans, J.; Zamboni, R.; Nathaniel, D.; Leveille, C.; Ford-Hutchinson, A. W. Prostaglandins 1985, 30, 981.
9. For total synthesis of LTB4, see; (a) Corey, E. J.; Marfat, A.; Goto, G.; Brion, F. J. Am. Chem. Soc. 1980, 102, 7984.
10. Corey, E. J.; Marfat, A.; Munroe, J.; Kim, K. S.; Hopkins, P. B.; Brion, F. Tetrahedron Lett. 1981, 22, 1077.
11. Guindon, Y.; Zamboni, R.; Lau, C.-K.; Rokach, J. Tetrahedron Lett. 1982, 23, 739.
12. Zamboni, R.; Rokach, J. Tetrahedron Lett. 1982, 23, 2631.
13. Mills, L. S.; North, P. C. Tetrahedron Lett. 1983, 24, 409.
14. Nicolaou, K. C.; Zipkin, R. E.; Dolle, R. E.; Harris, B. D. J. Am. Chem. Soc. 1984, 106, 3548.
15. Han, C.-Q.; DiTullio, D.; Wang, Y.-F.; Sih, C. J. J. Org. Chem. 1986, 51, 1253.
16. Le Merrer, Y.; Gravier, C.; Languin-Micas, D.; Depezay, J. C. Tetrahedron Lett. 1986, 27, 4161.
17. Guindon, Y.; Delorme, D.; Lau, C. K.; Zamboni, R. J. Org. Chem. 1988, 53, 267.
18. Le Merrer, Y.; Gravier-Pelletier, C.; Micas-Languin, D.; Mestre, F.; Dureault, A.; Depezay, J.-C. J. Org. Chem. 1989. 54. 2409.
19. For total synthesis of 20-OH-LTB4, see: (a) Zamboni, R.; Rokach, J. Tetrahedron Lett. 1982, 23, 4751.
20. Nicolaou, K. C.; Chung, Y. S.; Hernandez, P. E.: Taffer, I. M.; Zipkin, R. E. Tetrahedron Lett. 1986, 27, 1881.
21. For total synthesis of LTB3, see: (a) Spur, B.; Crea, A.; Peters, W. Arch. Pharm. (Weinheim) 1985, 318, 225.
22. Guillerm, D.; Linstrumelle, G. Tetrahedron Lett. 1986, 27. 5857.
23. For a preliminary communication, see: Kobayashi, Y.; Shimazaki, T.; Sato, F. Tetrahedron Lett. 1987, 28, 5849.
24. Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
25. Kitano, Y.; Matsumoto, T.; Sato, F. Tetrahedron 1988, 44, 4073:
26. J. Chem. Soc. Chem. Commun. 1986. 1323.
27. Kitano, Y.; Matsumoto, T.; Wakasa, T.; Okamoto, S.; Shimazaki, T.; Kobayashi, Y.; Sato, F.; Miyaji, K.; Arai, K. Tetrahedron Lett. 1987, 28. 6351.
28. Ohkawa, S.; Terao, S. J. Takeda Res. Lab. 1983, 42, 13.
29. Burgstahler, A. W.; Weigel, L. O.; Shaefer, C. G. Synthesis 1976, 767.
30. Aluminum anion 9 (M = AlEt2) gave a better yield of dl-10 than lithium anion 9 (M = Li).
31. Okamoto, S.; Shimazaki, T.; Kobayashi, Y.; Sato, F. Tetrahedron Lett. 1987, 28, 2033.
32. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
33. Takahashi, S.,; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
34. Ratovelomana, V.; Linstrumelle, G. Synth. Commun. 1981, 11, 917.
35. Nicolaou, K. C.; Webber, S. E. J. Am. Chem. Soc. 1984, 106, 5734.
36. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
37. Sato, F. J. Organomet. Chem. 1985, 285, 53.
38. Sato, F.; Ishikawa, H.: Sato, M. Tetrahedron Lett. 1981. 22. 85.
39. Winter, M. Helv. Chim. Acta 1963. 46. 1792.
40. Epoxidation of (R)-17 by using t-BuOOH/VO(acac)2 or t- BuOOH/Ti(O-i-Pr)4 afforded the diepoxide in addition to the desired monoepoxide.
41. Mitsunobu, O., Synthesis 1981, 1.
42. Jung, M. E.; Gaede, B. Tetrahedron 1979. 35. 621.
43. Luo, F.-T.; Negishi, E. J. Org. Chem. 1985, 50, 4762.
44. Ford-Hutchinson, A. W.; Rackham, A.; Zamboni, R.; Rokach, J.; Roy, S. Prostaglandins 1983, 25, 29.
45. Leblanc, Y.; Fitzsimmons, B. J.; Zamboni, R.; Rokach, J. J. Org. Chem. 1988, 53. 265.
46. Shimazaki, T.; Kobayashi, Y.; Sato, F.; Iwama, T.; Shikada, K. Prostaglandins 1990, 39, 459.
47. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
48. Brown, H. C. Organic Synthesis via Boranes; Wiley: New York, 1975: pp 29–31.
49. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: New York, 1981; pp 55–56.
50. Cunico, R. F.; Clayton, F. J. J. Org. Chem. 1976, 41, 1480.