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0035477181
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The current synthesis is applicable to the natural enantiomer of the bengamides as the antipode of ketone 1 (ent-1) is known:
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The current synthesis is applicable to the natural enantiomer of the bengamides as the antipode of ketone 1 (ent-1) is known:. Forsyth C.J., Hao J., and Aiguadé J. Angew. Chem., Int. Ed. 40 (2001) 3663-3667
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36049005790
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note
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3N. Pure 6 could be obtained (as a mixture of diastereomers) by chromatography on Iatrobeads 6RS-8060, available from Mitsubishi Kagaku Iatron, Inc.
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27
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36048986566
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note
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The benzoate protecting groups, while not necessary for completion of the synthesis, are necessary to achieve the desired selectivity in the aldol reaction (see Ref. 4).
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28
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36049035788
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note
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For ease of isolation, an N-phenyl amide was selected for the current exercise but it is expected that a diverse array of amines could be used for this process, including caprolactam derivatives which would lead to the bengamide family.
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30
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note
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It is also likely that the alkoxide acts as a base in an intramolecular fashion, since recovered starting material is always diastereomerically pure.
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