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The spiroketals 20 and 21 were prepared by the nucleophilic additions of Grignard reagent or dianion prepared by Cohen's procedure to the corresponding lactone, see ref. 19 .
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46
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85119738635
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The preparation of spiroketals 22 and 23 were described in the following section.
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85119762844
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α epimer of 21 was detected on GC-analysis of recovered spiroketals. In the similar reaction at -78°C, however, no isomer of 21 was detected.
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85119723894
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The desired diastereomer ( S configuration): δ (ppm) -0.021 and 0.017. The undesired diastereomer ( R configuration): δ (ppm) -0.006 and 0.025.
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85119763768
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The natural form and the 7S-isomer were obtained slightly with the recovery of the starting 2 R , 4 S -isomer mainly and decompositions decreased their yields
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