Department of Chemical and Biological Engineering/Organic Chemistry, Chalmers University of Technology, SE-412 96 Gothenburg, Sweden.
Org Lett. 2011 Aug 19;13(16):4458-61. doi: 10.1021/ol201812n. Epub 2011 Jul 25.
The first total synthesis of the dimeric alkaloid pigment scytonemin is described. The key transformations in its synthesis from 3-indole acetic acid are a Heck carbocyclization and a Suzuki-Miyaura cross-coupling, orchestrated in a stereospecific tandem fashion, followed by a biosynthetically inspired oxidative dimerization. The tandem sequence generates a tetracyclic (E)-3-(arylidene)-3,4-dihydrocyclopenta[b]indol-2(1H)-one that is subsequently dimerized into the unique homodimeric core structure of scytonemin.
首次全合成二聚生物碱色素 Scytonemin。其从 3-吲哚乙酸合成的关键转化是 Heck 碳环化和 Suzuki-Miyaura 交叉偶联，以立体定向串联方式进行，随后进行生物合成启发的氧化二聚化。串联序列生成四环（E）-3-（亚芳基）-3,4-二氢环戊并[b]吲哚-2(1H)-酮，随后二聚化成 Scytonemin 的独特同二聚核结构。
