Liu Kai, Taylor Richard E, Kartika Rendy
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.
Org Lett. 2006 Nov 9;8(23):5393-5. doi: 10.1021/ol0623318.
[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.
[结构：见正文] 已开发出一种通过对高烯丙基烷氧基甲基醚进行亲电活化来形成顺式-1,3-二醇单醚和二醚的全新策略性方法。所得的类聚酮合成片段产率良好且具有出色的立体控制。提出了一种椅状过渡态来解释高立体选择性。改变反应后处理条件可有效生成聚酮天然产物中常见的含单醚和二醚的结构单元。
