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The stereochemistries associated with the ethyl acetal center in each of compounds 28a and 28b have not been determined but we have confirmed that common intermediate 3 in Scheme 10 was similarly obtained from each isomer.
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10844243880
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note
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We initially assumed the stereochemistry of the newly generated hydroxyl group of the major alcohol 7 a to be β since the hydride attack seemed most likely to occur from the convex site of ketone 6. The stereochemistry at C12 in compound 7a, however, was later found to be α as shown in Figure 3 by NOESY analysis of the final compound 2.
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119
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note
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A trace of Z-isomer of olefin 4 was also formed.
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note
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The present synthesis consists of a total of 40 steps from lactone 10 with an overall yield of ca. 0.45%. The overall yield was calculated on the basis of the combined yield of 2 obtained from both 28a and 28b although the route from 28a to 3 appears only in this paper.
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