title: Electrophile-induced ether transfer: a new approach to polyketide structural units.
abstract: [Structure: see text] A strategically novel approach to the formation of syn-1,3-diol mono- and diethers through electrophilic activation of homoallylic alkoxymethyl ethers has been developed. The resulting polyketide-like synthetic fragments are generated in good yield and with excellent stereocontrol. A chairlike transition state is proposed to account for the high stereoselectivity. Varying the conditions of the reaction workup results in the efficient generation of mono- and diether containing structural units common to polyketide natural products.
authors.affiliation: Department of Chemistry and Biochemistry and the Walther Cancer Research Center, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA.
authors.forename: Kai
authors.initials: K
authors.lastname: Liu
authors.forename: Richard E
authors.initials: RE
authors.lastname: Taylor
authors.forename: Rendy
authors.initials: R
authors.lastname: Kartika
mesh_terms: D004987:Ethers / Q000737:chemistry*; D018942:Macrolides / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D004987:Ethers; D018942:Macrolides