佩里考宁 A 的全合成。
Total Synthesis of Pericoannosin A.
机构信息
Institute for Organic Chemistry and Centre of Biomolecular Drug Research (BMWZ), Leibniz Universität Hannover , Schneiderberg 1B , D-30167 Hannover , Germany.
Helmholtz Centre for Infection Research (HZI) , Inhoffenstrasse 7 , D-38124 Braunschweig , Germany.
出版信息
Org Lett. 2018 Aug 3;20(15):4475-4477. doi: 10.1021/acs.orglett.8b01768. Epub 2018 Jul 13.
The first total synthesis of pericoannosin A (1) containing 15 steps in the longest linear sequence with an overall yield of 5.5% is reported. The hybrid peptide-polyketide was isolated from the endophytic fungus Periconia sp. F-31 and bears a unique tricyclic core structure. The key steps are a glycolate aldol reaction and a Diels-Alder reaction utilizing an Evans auxiliary for controlling the stereochemistry. Furthermore, a late-stage equilibration was employed.
首次报道了含有 15 步最长线性序列的全合成方法，总收率为 5.5%，成功合成了佩里考宁 A（1）。该杂合肽聚酮来源于内生真菌 Periconia sp. F-31，具有独特的三环核心结构。关键步骤包括利用 Evans 辅助进行立体控制的甘醇醛缩合反应和 Diels-Alder 反应。此外，还采用了晚期平衡反应。
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