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The four-component assembly of 7, 29, 19, and 20 in one pot turned out to be impracticable (giving silylated 33 in <15% yield)
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The four-component assembly of 7, 29, 19, and 20 in one pot turned out to be impracticable (giving silylated 33 in <15% yield).
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81
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The undesired diastereomer (7% yield) formed by the alkylation was separated by silica gel chromatography
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The undesired diastereomer (7% yield) formed by the alkylation was separated by silica gel chromatography.
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82
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Crystallographic data for CCDC-699152 (15), CCDC-669153 (silylated derivative of 37a), CCDC-699151 (mono-p-bromobenzoate of 17b), and CCDC-699155 (45) were reported in ref 24. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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Two endoperoxides, 43 and 45, exhibited moderate antimalarial activities, with IC50 values 2.67 and 8.25 μg/mL, respectively, while the others, including 44 and trioxane 49, were shown to be inactive (IC50 = >12.5 μg/mL); see Supporting Information
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