title: 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 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.
authors.affiliation: Department of Chemistry, Williams College, Williamstown, Massachusetts 01267, United States. tsmith@williams.edu
authors.forename: Thomas E
authors.initials: TE
authors.lastname: Smith
authors.forename: Sarah J
authors.initials: SJ
authors.lastname: Fink
authors.forename: Zebulon G
authors.initials: ZG
authors.lastname: Levine
authors.forename: Kerani A
authors.initials: KA
authors.lastname: McClelland
authors.forename: Adrian A
authors.initials: AA
authors.lastname: Zackheim
authors.forename: Mary E
authors.initials: ME
authors.lastname: Daub
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D018942:Macrolides; C516408:tedanolide C