Electrophile-induced ether transfer: A new approach to polyketide structural units
Electrophile-induced ether transfer: A new approach to polyketide structural units
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DOI：
10.1021/ol0623318
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发表时间：
2006-11-09
期刊：
影响因子：
5.2
通讯作者：
Kartika, Rendy
中科院分区：
文献类型：
--
作者：
Liu, Kai;Taylor, Richard E.;Kartika, Rendy
[图形]已经开发了通过高烯丙基烷氧基甲基醚的亲电活化形成顺式-1，3-二醇单醚和二醚的战略性新方法。所得到的聚酮样合成片段以良好的产率和优异的立体控制产生。一个椅子状的过渡态，建议占高立体选择性。改变反应后处理的条件导致有效地产生聚酮化合物天然产物共有的含有单醚和二醚的结构单元。
[GRAPHICS]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.