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Stereochemically versatile synthesis of the C1-C12 fragment of tedanolide C.

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 ?-ketoester dianion to an ?,?-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.

SUBMITTER: Smith TE

PROVIDER: S-EPMC3312041 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

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Stereochemically versatile synthesis of the C1-C12 fragment of tedanolide C.

Smith Thomas E TE Fink Sarah J SJ Levine Zebulon G ZG McClelland Kerani A KA Zackheim Adrian A AA Daub Mary E ME

Organic letters 20120229 6

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 hi ...[more]

PMID: 22375885

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