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We recently reported a strategy to access E-type isoprostane isomers: Pinot, E, Guy, A, Fournial, A, Balas, L, Rossi, J. C, Durand, T. J. Org. Chem. 2008, 73, 3063
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We recently reported a strategy to access E-type isoprostane isomers: Pinot, E.; Guy, A.; Fournial, A.; Balas, L.; Rossi, J. C.; Durand, T. J. Org. Chem. 2008, 73, 3063.
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Hodgson, D.M.1
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Iimori, T.1
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25
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11144356580
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ter Halle, R.; Bernet, Y.; Billard, S.; Bufferne, C.; Carlier, P.; Delaitre, C.; Flouzat, C.; Humblot, G.; Laigle, J. C.; Lombard, P.; Wilmouth, S. Org. Process Res. Dev. 2004, 8, 283.
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ter Halle, R.1
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Flouzat, C.7
Humblot, G.8
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Wilmouth, S.11
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Bouzemi, N.1
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Aribi-Zouioueche, L.3
Fiaud, J.C.4
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27
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60949103213
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The ee's were determined by converting alcohols into their corresponding 2,4-dinitrobenzoate derivatives and by chiral HPLC analysis (see the Supporting Information).
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The ee's were determined by converting alcohols into their corresponding 2,4-dinitrobenzoate derivatives and by chiral HPLC analysis (see the Supporting Information).
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28
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0034625897
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Nicolaou, K. C.; Zhong, Y. L.; Baran, P. S. J. Am. Chem. Soc. 2000, 122, 7596.
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Nicolaou, K.C.1
Zhong, Y.L.2
Baran, P.S.3
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29
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37049070648
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Enone 5 was previously obtained in three steps from 4 by palladium-induced oxidation of the silyl enol ether obtained from the corresponding ketone in 55% yield; see: Parkes, K. E. B.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1988, 1119.
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Enone 5 was previously obtained in three steps from 4 by palladium-induced oxidation of the silyl enol ether obtained from the corresponding ketone in 55% yield; see: Parkes, K. E. B.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1988, 1119.
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31
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84985279173
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The stereochemistry of cis- and trans-1,3-diols 8a was confirmed by NMR experiments and by reported NMR data of trans-8a; see: Weinges, K.; Haremsa, S. Liebigs Ann. Chem. 1987, 679.
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The stereochemistry of cis- and trans-1,3-diols 8a was confirmed by NMR experiments and by reported NMR data of trans-8a; see: Weinges, K.; Haremsa, S. Liebigs Ann. Chem. 1987, 679.
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32
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0029069807
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It is reported that oxidation of diols by IBX afforded only lactols. For 1,4-diol to lactol oxidation by IBX, see: Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 3485.
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It is reported that oxidation of diols by IBX afforded only lactols. For 1,4-diol to lactol oxidation by IBX, see: Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 3485.
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33
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0037062896
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Suzuki, T.; Morita, K.; Tsuchida, M.; Hiroi, K. Org. Lett. 2002, 4, 2361.
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(2002)
Org. Lett
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Suzuki, T.1
Morita, K.2
Tsuchida, M.3
Hiroi, K.4
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34
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0027944734
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2tIsoP 1 based on an approach developed by Rokach; see: Hwang, S. W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829.
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2tIsoP 1 based on an approach developed by Rokach; see: Hwang, S. W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829.
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35
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60949107979
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Two side products were also isolated; a coeluting compound with 16 attributed to the E isomer and a compound corresponding to a silyl migration to the primary alcohol (see the Supporting Information).
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Two side products were also isolated; a coeluting compound with 16 attributed to the E isomer and a compound corresponding to a silyl migration to the primary alcohol (see the Supporting Information).
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36
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60949087699
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Absolute configurations were determinated after completion of the synthesis to known 15-F2t-ISoP 1 and its 15-epimer and by NMR correlation of known 17a see ref 23
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2t-ISoP 1 and its 15-epimer and by NMR correlation of known 17a (see ref 23).
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38
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60949086085
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Yield given from a 1:1 mixture 17a and 17b after separation of triol epimers (see the Supporting Information).
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Yield given from a 1:1 mixture 17a and 17b after separation of triol epimers (see the Supporting Information).
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