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14
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A single total synthesis of the racemate was reported. See: (a) Kishi, Y.; Aratani, M.; Fukuyama, T.; Nakatsubo, F.; Goto, T.; Inoue, S.; Tanino, H.; Sugiura, S.; Kakoi, H. J. Am. Chem. Soc. 1972, 94, 9217.
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Kakoi, H.9
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19
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0015526373
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(b) Kishi, Y.; Fukuyama, T.; Aratani, M.; Nakatsubo, F.; Goto, T.; Inoue, S.; Tanino, H.; Sugiura, S.; Kakoi, H. J. Am. Chem. Soc. 1972, 94, 9219.
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Speslacis, J.1
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27
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0043006793
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The numbering used in this paper corresponds to that of tetrodotoxin
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The numbering used in this paper corresponds to that of tetrodotoxin.
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28
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0041504030
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note
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7 while hydrolysis of 8 under the same conditions did not proceed. Attempted one-step conversion of 8 to 9 under forcing hydrolytic conditions failed.
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29
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0042005080
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note
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The protective group was critical not only for the further functionalization, but for final successful deprotection.
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30
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0017575580
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(a) Isobe, M.; Iio, H.; Kawai, T.; Goto, T. Tetrahedron Lett. 1977, 703.
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0018361165
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(b) Iio, H.; Isobe, M.; Kawai, T.; Goto, T. Tetrahedron 1979, 35, 941.
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32
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0042005078
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note
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1H NMR).
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33
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0042505789
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note
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Determination of the configuration of C-9 is included in Supporting Information.
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35
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0042005079
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note
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The TMS group of acetylene was removed when the crude ynone was dissolved in MeOH dried over 3 Å molecular sieves.
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36
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0042005076
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note
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We found that a small amount of water drove the in situ deprotection of TMS ether and subsequent acetylation to give 14 in one pot.
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37
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0043006792
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note
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A series of these reactions were performed without purification, because of the instability of the intermediates.
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38
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2542433188
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Carisen, P. H.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
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40
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0043006791
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note
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Configurations of the C-4 position of 16a and 16b were established to be S and R by coupling constants between H-4 and H-4a (0 and 4 Hz, respectively). See ref 8.
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41
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0042005077
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note
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Details will be disclosed in a full account of this study.
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42
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0033119493
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Nishikawa, T.; Ohyabu, N.; Yamamoto, N.; Isobe, M. Tetrahedron 1999, 55, 4325.
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43
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0042505788
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note
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Structures of the products have not been fully elucidated, because of the instability.
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44
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0001008307
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0037050416
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48
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0041504029
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note
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1H NMR).
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