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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.

SUBMITTER: Liu K

PROVIDER: S-EPMC2613644 | biostudies-literature | 2006 Nov

REPOSITORIES: biostudies-literature

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

Liu Kai K Taylor Richard E RE Kartika Rendy R

Organic letters 20061101 23

[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 containi ...[more]

PMID: 17078726

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