4.8 Article

Stereochemically Versatile Synthesis of the C1-C12 Fragment of Tedanolide C

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ORGANIC LETTERS
卷 14, 期 6, 页码 1452-1455

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AMER CHEMICAL SOC
DOI: 10.1021/ol300194x

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  1. National Cancer Institute [R15CA132072]
  2. Pfizer

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A flexible synthesis of the C1-C12 fragment of Tedanolide C has been accomplished in eight steps from 2-methyl-2,4-pentadienal. Asymmetric hydroformylation of a 1,3-diene allows for the late-stage generation of either C10 epimer with complete catalyst control. Diastereoselective addition of an isobutyryl beta-ketoester dianion to an alpha,beta-disubstituted chiral aldehyde sets the C5 stereochemistry while installing the geminal dimethyl unit. Differential protection of a syn-1,3-diol is performed as a highly efficient single-pot operation.

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