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Total synthesis of tedanolide: Ehrlich, G.; Hassfeld, J.; Eggert, U.; Kalesse, M. J. Am. Chem. Soc. 2006, 128, 14038.
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(a) Total synthesis of tedanolide: Ehrlich, G.; Hassfeld, J.; Eggert, U.; Kalesse, M. J. Am. Chem. Soc. 2006, 128, 14038.
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7503. For reviews, see
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(a) Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503. For reviews, see:
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Formation and Addition Reactions of Enol Ethers
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Asymmetric Synthesis with Enol Ethers
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Gennari, C.1
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38349173757
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Ethylmagnesium bromide was added to the aldehyde 8 followed by Dess-Martin oxidation to the ketone. Reductive ring-opening with zinc in acetic acid and silylation of the diol with TBSCl gave 7.
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Ethylmagnesium bromide was added to the aldehyde 8 followed by Dess-Martin oxidation to the ketone. Reductive ring-opening with zinc in acetic acid and silylation of the diol with TBSCl gave 7.
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24
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33845373936
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38349100639
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Extensive decoupling experiments were carried out to ensure the identity of the indicated protons in all the acetonides
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Extensive decoupling experiments were carried out to ensure the identity of the indicated protons in all the acetonides.
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28
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34249998647
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Cazeau, P.; Duboudin, F.; Moulines, F.; Babot, O.; Dunogues, J. Tetrahedron 1987, 43, 2088.
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Denmark, S.E.1
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30
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38349187776
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These calculations were done on a simpler model system where the enol silyl ether was replaced by an enol, the OTBDPS group by an OH, and the OBn by an OMe group with the R group being ethyl R, Et
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These calculations were done on a simpler model system where the enol silyl ether was replaced by an enol, the OTBDPS group by an OH, and the OBn by an OMe group with the R group being ethyl (R = Et).
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