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For experimental details, see Supporting Information.
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27544508197
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note
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The absolute configuration of C7 alcohol was confirmed by Mosher ester analysis. See Supporting Information for details.
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26
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27544488952
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note
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1H NMR. Recovery of starting material as the 2Z-alkene showed a similar ratio of C10 diastereomers.
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27
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84982433710
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2-ZrHCl, followed by elimination at C10-C11, may lead to partial epimerization. For precedent of this mechanism, see: (a) Schwartz, J.; Labinger, J. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
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