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

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journal contribution
posted on 16.03.2012 by Thomas E. Smith, Sarah J. Fink, Zebulon G. Levine, Kerani A. McClelland, Adrian A. Zackheim, Mary E. Daub
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.