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26
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0343899370
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In preparation
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Mukai, C.; Yamaguchi, S.; Miyakoshi, N.; Sugimoto, Y.; Kasamatsu, E.; Hanaoka, M. In preparation.
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Mukai, C.1
Yamaguchi, S.2
Miyakoshi, N.3
Sugimoto, Y.4
Kasamatsu, E.5
Hanaoka, M.6
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30
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0342593668
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note
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Mineral acids and organic acids were also used instead of a Lewis acid. However, the formation of oxocanes could not be detected in the reaction mixture.
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31
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0342593669
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note
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8-protons enabled us to confirm the depicted structure of 21.
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32
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0343027806
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note
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When the methyl and benzyl congeners 30 and 31 were independently submitted to the reaction conditions described for the transformation of 19 into 20, the corresponding oxocane derivatives, 20 and 32, could not be detected in the reaction mixture. These results can tentatively be interpreted in terms of the lack of a cationic intermediate like 22. Therefore, it might be concluded that the β-trimethylsilylmethyl group at the C-2 position of the tetrahydrofuran ring is mandatory for conversion of 19 to 20. The details of these results will be reported in the near future.
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