Total synthesis of zincophorin methyl ester. Stereocontrol of 1,2-induction using sterically hindered enoxysilanes through Biotage Isolera耐士科技

2015/02/12   下载量： 5 次

方案摘要

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应用领域 制药/生物制药
检测样本 化药新药研发
检测项目 其他>方法开发
参考标准 GB/T 8****

Reported herein is the total synthesis of zincophorin methyl ester, a polyketide ionophore. Of particular interest is the use of sterically hindered nucleophiles to surmount the unfavorable stereochemical outcome, leading to acetate aldol adducts, in nucleophilic addition to the aldehyde derived from propionates. The approach is based on the addition of an enoxysilane (bearing a removable phenylselenide moiety) to generate selectively FelkineAnh adducts in a BF3,OEt2-mediated Mukaiyama aldol reaction. Subsequent reduction of the selenide group led to the corresponding syn-aldol acetate motif, and this approach was applied to induce selectively the C12eC13 relationship of zincophorin.

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