Title

Electrophile-induced ether transfer: A new approach to polyketide structural units

Document Type

Article

Publication Date

11-9-2006

Abstract

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. © 2006 American Chemical Society.

Publication Source (Journal or Book title)

Organic Letters

First Page

5393

Last Page

5395

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