Stereochemically versatile synthesis of the C1-C12 fragment of tedanolide C |
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Authors: | Smith Thomas E Fink Sarah J Levine Zebulon G McClelland Kerani A Zackheim Adrian A Daub Mary E |
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Institution: | Department of Chemistry, Williams College, Williamstown, Massachusetts 01267, United States. tsmith@williams.edu |
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Abstract: | 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 β-ketoester dianion to an α,β-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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