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1
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For reviews, see: a
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For reviews, see: (a) Serhan, C. N.; Chiang, N.; Van Dyke, T. E. Nat. Rev. Immunol., 2008, 8, 349-361.
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Serhan, C.N.1
Chiang, N.2
Van Dyke, T.E.3
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3
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12344321136
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(a) 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.
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J. Exp. Med
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Arita, M.1
Bianchini, F.2
Aliberti, J.3
Sher, A.4
Chiang, N.5
Hong, S.6
Yang, R.7
Petasis, N.A.8
Serhan, C.N.9
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4
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34250357688
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(b) Schwab, J. M.; Chiang, N.; Arita, M.; Serhan, C. N. Nature 2007, 447, 869-875.
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Nature
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Schwab, J.M.1
Chiang, N.2
Arita, M.3
Serhan, C.N.4
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5
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33751020561
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Tjonahan, E.; Oh, S. F.; Siegelman, J.; Elangovan, S.; Percarpio, K. B.; Hong, S.; Arita, M.; Serhan, C. N. Chem. Biol. 2006, 13, 1193-1202.
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Chem. Biol
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Tjonahan, E.1
Oh, S.F.2
Siegelman, J.3
Elangovan, S.4
Percarpio, K.B.5
Hong, S.6
Arita, M.7
Serhan, C.N.8
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6
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7244242688
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Total syntheses of resolvins E1 were disclosed in ref 2a. Total synthesis of resolvins D2 and D5 were reported. (a) Rodriguez, A. R.; Spur, B. W. Tetrahedron Lett. 2004, 45, 8717-8720.
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Total syntheses of resolvins E1 were disclosed in ref 2a. Total synthesis of resolvins D2 and D5 were reported. (a) Rodriguez, A. R.; Spur, B. W. Tetrahedron Lett. 2004, 45, 8717-8720.
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-
-
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8
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0025914829
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For a review of syntheses of eicosanoids, see: c
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For a review of syntheses of eicosanoids, see: (c) Nicolaou, K. C.; Ramphal, J. Y.; Petasis, N. A.; Serhan, C. N. Angew. Chem., Int. Ed. 1991, 30, 1100-1116.
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Angew. Chem., Int. Ed
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Nicolaou, K.C.1
Ramphal, J.Y.2
Petasis, N.A.3
Serhan, C.N.4
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9
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0001414464
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For rationalization of torquoselectivity, see: a
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For rationalization of torquoselectivity, see: (a) Rudolf, K.; Spell-meyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 3708-3710.
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(1987)
J. Org. Chem
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Rudolf, K.1
Spell-meyer, D.C.2
Houk, K.N.3
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10
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0000203981
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(b) Niwayama, S.; Kallel, E. A.; Spellmeyer, D. C.; Sheu, C.; Houk, K. N. J. Org. Chem. 1996, 61, 2813-2825.
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(1996)
J. Org. Chem
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Niwayama, S.1
Kallel, E.A.2
Spellmeyer, D.C.3
Sheu, C.4
Houk, K.N.5
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11
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0001261240
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(c) Dolvier, W. R., Jr.; Koroniak, H.; Houk, K. N.; Sheu, C. Acc. Chem. Res. 1996, 29, 471-477.
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Acc. Chem. Res
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Dolvier Jr., W.R.1
Koroniak, H.2
Houk, K.N.3
Sheu, C.4
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12
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0026565383
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Wallace demonstrated selective ring opening of cyclobutene aldehydes and substrate-controlled stereoselective introductions of various carbon nucleophiles to disubstituted cyclobutenes: (a) Binns, F, Hayes, R, Ingham, S, Saengchantara, S. T, Turner, R. W, Wallace, T. W. Tetrahedron 1992, 48, 515-530
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Wallace demonstrated selective ring opening of cyclobutene aldehydes and substrate-controlled stereoselective introductions of various carbon nucleophiles to disubstituted cyclobutenes: (a) Binns, F.; Hayes, R.; Ingham, S.; Saengchantara, S. T.; Turner, R. W.; Wallace, T. W. Tetrahedron 1992, 48, 515-530.
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13
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0028303651
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(b) Hodgetts, K. J.; Wallis, C. J.; Wallace, T. W. Tetrahedron Lett. 1994, 35, 4645-4648.
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(1994)
Tetrahedron Lett
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, pp. 4645-4648
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Hodgetts, K.J.1
Wallis, C.J.2
Wallace, T.W.3
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15
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0030069041
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(d) Binns, F.; Hayes, R.; Hodgetts, K. J.; Saengchantara, S. T.; Wallace, T. W.; Wallis, C. J. Tetrahedron 1996, 52, 3631-3658.
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(1996)
Tetrahedron
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Binns, F.1
Hayes, R.2
Hodgetts, K.J.3
Saengchantara, S.T.4
Wallace, T.W.5
Wallis, C.J.6
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16
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0033548151
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Enantioselective syntheses of (+)- and (-)-6 by enzymatic resolution were reported: Gourdel-Martin, M.-E.; Comoy, C.; Huet, F. Tetrahedron: Asymmetry 1999, 10, 403-404. See also ref 6b and 6c.
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Enantioselective syntheses of (+)- and (-)-6 by enzymatic resolution were reported: Gourdel-Martin, M.-E.; Comoy, C.; Huet, F. Tetrahedron: Asymmetry 1999, 10, 403-404. See also ref 6b and 6c.
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17
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0003590275
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(a) Koltzenburg, G.; Fuss, P. G.; Leitich, J. Tetrahedron Lett. 1966, 29, 3409-3414.
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(1966)
Tetrahedron Lett
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Koltzenburg, G.1
Fuss, P.G.2
Leitich, J.3
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19
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0032892995
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(c) Gauvry, N.; Comoy, C.; Lescop, C.; Huet, F. Synthesis 1999, 574-576.
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(1999)
Synthesis
, pp. 574-576
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Gauvry, N.1
Comoy, C.2
Lescop, C.3
Huet, F.4
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20
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33845420420
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For a review of synthetic applications of lactone 6 and derivatives, see: Gauvry, N.; Lescop, C.; Huet, F. Eur. J. Org. Chem. 2006, 520, 7-5218.
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For a review of synthetic applications of lactone 6 and derivatives, see: Gauvry, N.; Lescop, C.; Huet, F. Eur. J. Org. Chem. 2006, 520, 7-5218.
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21
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54749152753
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Oh, S. H.; Rho, H. S.; Lee, J. W.; Lee, J. E.; Youk, S. H.; Chin, J.; Song, C. E. Angew. Chem., Int. Ed. 2008, 47, 7872-7875.
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(2008)
Angew. Chem., Int. Ed
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, pp. 7872-7875
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Oh, S.H.1
Rho, H.S.2
Lee, J.W.3
Lee, J.E.4
Youk, S.H.5
Chin, J.6
Song, C.E.7
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22
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0041378031
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For a review of asymmetric alcoholysis of cyclic anhydrides, see
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For a review of asymmetric alcoholysis of cyclic anhydrides, see: Chen, Y.; McDaid, P.; Deng, L. Chem. Rev. 2003, 103, 2965-2983.
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(2003)
Chem. Rev
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Chen, Y.1
McDaid, P.2
Deng, L.3
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23
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68949114873
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1H NMR spectra of the MTPA ester of alcohol 11.
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1H NMR spectra of the MTPA ester of alcohol 11.
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24
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68949136057
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Absolute configuration of lactone 6 was deduced from the report of Wallace and co-workers, see ref 6d
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Absolute configuration of lactone 6 was deduced from the report of Wallace and co-workers, see ref 6d.
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26
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33847086948
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Brown, H. C.; Kim, S. C.; Krishnamurthy, S. J. Org. Chem. 1980, 45, 1-12.
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(1980)
J. Org. Chem
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Brown, H.C.1
Kim, S.C.2
Krishnamurthy, S.3
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27
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33845378873
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Wenkert, D.; Ferguson, S. B.; Porter, B.; Qvarnstrom, A.; McPhail, A. T. J. Org. Chem. 1985, 50, 4114-4119.
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J. Org. Chem
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Wenkert, D.1
Ferguson, S.B.2
Porter, B.3
Qvarnstrom, A.4
McPhail, A.T.5
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28
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2142858450
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Stereochemistries at C5 and C18 positions were unambiguously determined by the modified Moshers' method. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096. See Supporting Information for the detailed procedure.
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Stereochemistries at C5 and C18 positions were unambiguously determined by the modified Moshers' method. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096. See Supporting Information for the detailed procedure.
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29
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68949149562
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E,Z-Dienes 20 and 24 were easily isomerized into E,E-diene upon standing at room temperature. Thus, organic solution of the reaction mixture from the oxidation was directly used for the reduction
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E,Z-Dienes 20 and 24 were easily isomerized into E,E-diene upon standing at room temperature. Thus, organic solution of the reaction mixture from the oxidation was directly used for the reduction.
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30
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33845375225
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(a) Leblanc, Y.; Futzsimmons, B. J.; Adams, J.; Perez, F.; Rokach, J. J. Org. Chem. 1986, 51, 789-793.
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(1986)
J. Org. Chem
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Leblanc, Y.1
Futzsimmons, B.J.2
Adams, J.3
Perez, F.4
Rokach, J.5
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32
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68949131546
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3P gave only trace amount of the product 2.
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3P gave only trace amount of the product 2.
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33
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68949085834
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3Et gave the desired product as a single isomer; however, the yield was 23%.
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3Et gave the desired product as a single isomer; however, the yield was 23%.
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38
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33646554176
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Fujioka, H.; Okitsu, T.; Sawama, Y.; Murata, N.; Li, R.; Kita, Y. J. Am. Chem. Soc. 2006, 128, 5930-5938.
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(2006)
J. Am. Chem. Soc
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Fujioka, H.1
Okitsu, T.2
Sawama, Y.3
Murata, N.4
Li, R.5
Kita, Y.6
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