Electrophile-induced ether transfer: a new approach to polyketide structural units.
[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.
Liu
Kai
K
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.
Taylor
Richard E
RE
Kartika
Rendy
R
D004987:Ethers / Q000737:chemistry*; D018942:Macrolides / Q000737:chemistry*; D015394:Molecular Structure
D004987:Ethers; D018942:Macrolides