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0041771577
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note
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13C NMR, IR, and HRMS. Yields refer to isolated, chromatographically purified products.
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29
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0001584981
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0042773469
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note
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A diastereomeric mixture (1:1) of the secondary alcohols was also isolated (10%).
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32
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0041771576
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note
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Hydrolytic removal of the isopropylidene group in the TBDPS ether derived from 13 provided the corresponding diol in an unacceptable low yield.
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33
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0028858318
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35
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0043274761
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note
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In our hands, the yield of 20 increased when the reaction was conducted on a larger scale. Consequently, we were able to prepare 20 on a 15 g scale with complete diastereoselectivity.
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36
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0025819975
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Compound 21 had been synthesized by Boeckman et al. using a different route, see: Boeckman, R. K., Jr.; Charette, A. B.; Asberom, T.; Johnston, B. H. J. Am. Chem. Soc. 1991, 113, 5337-5353.
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39
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0042773468
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note
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The reductive opening of the TBDPS-protected acetal, prepared from 24 [(1) MPM acetal formation, (2) silyl ether (OTBDPS) formation], with DIBALH was accompanied by cleavage of the silyl ether.
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43
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0041771575
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note
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The overall yield of 6 from 8 was 23% and that from 19 was 16%. We prefer the second route because the isolation of 9 from other diastereomers by Chromatographic separation on silica gel was problematic in our case on a large-scale experiment.
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44
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37049090303
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De Meijere, A.4
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48
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0041771574
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note
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During a large-scale preparation of 29E, we encountered a tedious Chromatographic separation of 28E and 28Z.
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