Total syntheses of four possible stereoisomers of resolvin E3

Tetrahedron

Volumn 68, Issue 15, 2012, Pages 3210-3219

  Urabe, Daisuke ^a   Todoroki, Hidenori ^a   Masuda, Koji ^b   Inoue, Masayuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b SHIONOGI AND CO LTD   (Japan)

Author keywords

Convergent strategy; Eicosapentaenoic acid; Lipid mediators; Resolvin; Total synthesis

Indexed keywords

17,18 DIHYDROXY 5,8,11,13,15 EICOSAPENTAENOIC ACID; ALKENE; ALKYNE; ANTIINFLAMMATORY AGENT; COPPER; HYDROXYL GROUP; LIPID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HORNER WADSWORTH EMMONS REACTION; PRIORITY JOURNAL; REDUCTION; STEREOISOMERISM;

EID: 84858706517     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.02.045     Document Type: Article

References (40)

1. For reviews, see: (a) Serhan, C. N.; Chiang, N.; Van Dyke, T. E. Nat. Rev. Immunol. 2008, 8, 349-361;
2. (b) Serhan, C. N.; Chiang, N. Br. J. Pharmacol. 2008, 153, S200-S215.
3. Arita, M.; Bianchini, F.; Aliberti, J.; Sher, A.; Chiang, N.; Hong, S.; Yang, R.; Petasis, N. A.; Serhan, C. N. J. Exp. Med. 2005, 201, 713-722.
4. Tjonahen, E.; Oh, S. F.; Siegelman, J.; Elangovan, S.; Percarpio, K. B.; Hong, S.; Arita, M.; Serhan, C. N. Chem. Biol. 2006, 13, 1193-1202.
5. Schwab, J. M.; Chiang, N.; Arita, M.; Serhan, C. N. Nature 2007, 447, 869-875.
6. Isobe, Y.; Arita, M.; Matsueda, S.; Iwamoto, R.; Fujiwara, T.; Nakanishi, H.; Taguchi, R.; Masuda, K.; Sasaki, K.; Urabe, D.; Inoue, M.; Arai, H. J. Biol. Chem. 2012, doi:10.1074/jbc.M112.340612 [online early access].
7. Total syntheses of lipid mediators from our laboratory. Resolvin E2: (a) Ogawa, S.; Urabe, D.; Yokokura, Y.; Arai, H.; Arita, M.; Inoue, M. Org. Lett. 2009, 11, 3602-3605;
8. Maresin: (b) Sasaki, K.; Urabe, D.; Arai, H.; Arita, M.; Inoue, M. Chem. Asian J. 2011, 6, 534-543.
9. Total syntheses of resolvins from other laboratories. Resolvin E1: (a) Ogawa, N.; Kobayashi, Y. Tetrahedron Lett. 2009, 50, 6079-6082;
10. (b) Allard, M.; Barnes, K.; Chen, X.; Cheung, Y.-Y.; Duffy, B.; Heap, C.; Inthavongsay, J.; Johnson, M.; Krishnamoorthy, R.; Manley, C.; Steffke, S.; Varughese, D.; Wang, R.; Wang, Y.; Schwartz, C. E. Tetrahedron Lett. 2011, 52, 2623-2626;
11. Resolvin E2: (c) Kosaki, Y.; Ogawa, N.; Kobayashi, Y. Tetrahedron Lett. 2010, 51, 1856-1859;
12. Resolvin D2: (d) Rodríguez, A. R.; Spur, B. W. Tetrahedron Lett. 2004, 45, 8717-8720;
13. Resolvin D5: (e) Rodríguez, A. R.; Spur, B. W. Tetrahedron Lett. 2005, 46, 3623-3627;
14. For a review of syntheses of eicosanoids, see: (f) Nicolaou, K. C.; Ramphal, J. Y.; Petasis, N. A.; Serhan, C. N. Angew. Chem., Int. Ed. Engl. 1991, 30, 1100-1116.
15. (a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768-2771;
16. For a review on asymmetric dihydroxylation, see: (b) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
17. (a) Hayashi, Y.; Shoji, M.; Yamaguchi, J.; Sato, K.; Yamaguchi, S.; Mukaiyama, T.; Sakai, K.; Asami, Y.; Kakeya, H.; Osada, H. J. Am. Chem. Soc. 2002, 124, 12078-12079;
18. (b) Kandula, S. R. V.; Kumar, P. Tetrahedron: Asymmetry 2005, 16, 3268-3274;
19. (c) Carda, M.; Murga, J.; Falomir, E.; González, F.; Marco, J. A. Tetrahedron 2000, 56, 677-683.
20. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
21. Diols 10c and 10d were previously synthesized using other methods, see: (a) Dixon, D. J.; Ley, S. V.; Polara, A.; Sheppard, T. Org. Lett. 2001, 3, 3749-3752;
22. (b) Ley, S. V.; Dixon, D. J.; Guy, R. T.; Palomero, M. A.; Polara, A.; Rodríguez, F.; Sheppard, T. D. Org. Biomol. Chem. 2004, 2, 3618-3627.
23. (a) Lapitskaya, M. A.; Vasiljeva, L. L.; Pivnitsky, K. K. Synthesis 1993, 65-66;
24. (b) Durand, S.; Parrain, J.-L.; Santelli, M. Synthesis 1998, 1015-1018;
25. (c) Kandula, S. V.; Kumar, P. Tetrahedron Lett. 2003, 44, 1957-1958.
26. (a) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538-7539;
27. (b) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655-658;
28. (c) Allevi, P.; Tarocco, G.; Longo, A.; Anastasia, M.; Cajone, F. Tetrahedron: Asymmetry 1997, 8, 1315-1325;
29. For reviews on cyclic sulfites and sulfates chemistry, see: (d) Lohray, B. B. Synthesis 1992, 1035-1052;
30. (e) Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051-7091.
31. Kelly, A. M.; Pérez-Fuertes, Y.; Fossey, J. S.; Yeste, S. L.; Bull, S. D.; James, T. D. Nat. Protoc. 2008, 3, 215-219.
32. Fox, M. E.; Marino, J. P., Jr.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 5467-5480.
33. Caruso, T.; Spinella, A. Tetrahedron 2003, 59, 7787-7790.
34. Falck, J. R.; Barma, D. K.; Mohapatra, S.; Bandyopadhyay, A.; Reddy, K. M.; Qi, J.; Campbell, W. B. Bioorg. Med. Chem. Lett. 2004, 14, 4987-4990.
35. (a) Yoshida, Y.; Sakakura, Y.; Aso, N.; Okada, S.; Tanabe, Y. Tetrahedron 1999, 55, 2183-2192;
36. (b) Kessabi, J.; Beaudegnies, R.; Jung, P. M. J.; Martin, B.; Montel, F.; Wendeborn, S. Synthesis 2008, 655-659.
37. Nicolaou, K. C.; Veale, C. A.; Webber, S. E.; Katerinopoulos, H. J. Am. Chem. Soc. 1985, 107, 7515-7518.
38. No epimerization of hydroxy group at C17 position of aldehyde 6a-d was observed during the H.W.E. coupling.
39. Lindlar, H. Helv. Chim. Acta 1952, 35, 446-470.
40. Fujioka, H.; Okitsu, T.; Sawama, Y.; Murata, N.; Li, R.; Kita, Y. J. Am. Chem. Soc. 2006, 128, 5930-5938.