Organic Chemistry I, Saarland University, Campus Building C4.2, D-66123 Saarbrücken, Germany.
Helmholtz Institute for Pharmaceutical Research Saarland (HIPS), Saarland University, Campus Building C8.1, D-66123 Saarbrücken, Germany.
Org Lett. 2022 Apr 8;24(13):2541-2545. doi: 10.1021/acs.orglett.2c00701. Epub 2022 Mar 28.
The Matteson homologation was found to be a versatile tool for the construction of the linear polyketide side chain of meliponamycin and related compounds in only four steps. The ester dienolate version of this reaction allowed the introduction of the unsaturated ester moiety in a highly stereoselective fashion. Boronate oxidation/deoxygenation and Sharpless dihydroxylation are additional key steps in the stereoselective construction of this highly functionalized tetrahydropyran ring system, which is characteristic of this substance class.
马蒂森同系物被发现是构建美罗培南和相关化合物线性聚酮侧链的多功能工具，只需四步即可完成。该反应的酯烯醇酯形式允许以高度立体选择性的方式引入不饱和酯部分。硼酸氧化/脱氧和 Sharpless 双羟基化是立体选择性构建这种高度官能化的四氢吡喃环系的另外两个关键步骤，这是该物质类别的特征。
