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This result was confirmed by NOE studies performed on the cyclic diastereoisomers A and B. These compounds were smoothly prepared from the 80:20 mixture of 17a and 17b by sequential chemoselective hydrolysis of the tert-butyl ester group followed by cyclization with EDC and HOBT in DMF at room temperature, and finally separation by flash chromatography.
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4, a slightly reduced stereocontrol was observed (17a/17b, 70:30 vs 80:20 for the methyl ester and tert-butyl ester, respectively). This minimal dependence of the diastereoselectivity on the kind of lactate ester used seems to confirm this hypothesis.
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2 at -78 °C furnished a complex mixture of reaction products.
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It should be noted that the numbering scheme of 1 in Supporting Information is arbitrary, and that C-9 in the diagram corresponds to C-2.
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