University of Bergen , Department of Chemistry and Centre for Pharmacy, Allégt 41, NO-5007 Bergen, Norway.
Org Lett. 2015 Jan 2;17(1):122-5. doi: 10.1021/ol503348n. Epub 2014 Dec 16.
The first total synthesis of breitfussin A and B is described. The approach features two palladium-catalyzed cross-couplings installing the indole and pyrrole onto the oxazole core and selective lithiation/iodination of a common indole-oxazole fragment providing 2,4-diiodinated or 2-iodinated oxazoles as potential precursors for breitfussin A and B, respectively. An unexpected acid promoted deiodination was utilized in the synthesis of breitfussin B. Comparison of the synthetic material with previously reported spectral data of isolated breitfussin A and B verified the structure of the breitfussin framework.
本文描述了 breitfussin A 和 B 的首次全合成。该方法的特点是两个钯催化的交叉偶联反应，将吲哚和吡咯安装到恶唑核上，以及通过选择性锂化/碘化共同的吲哚-恶唑片段，分别提供 2,4-二碘化或 2-碘化恶唑作为 breitfussin A 和 B 的潜在前体。在 breitfussin B 的合成中利用了意想不到的酸促进脱碘化反应。合成材料与以前报道的分离 breitfussin A 和 B 的光谱数据进行比较，验证了 breitfussin 骨架的结构。
