Synthesis of Fijiolide A via an Atropselective Paracyclophane Formation,Journal of the American Chemical Society

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Synthesis of Fijiolide A via an Atropselective Paracyclophane Formation
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2015-08-27 , DOI: 10.1021/jacs.5b07964
Christoph Heinz ₁ , Nicolai Cramer ₁

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Fijiolide A is a secondary metabolite isolated from a marine-derived actinomycete and displays inhibitory activity against TNF-α-induced activation of NFκB, an important transcription factor and a potential target for the treatment of different cancers and inflammation related diseases. Fijiolide A is a glycosylated complex paracyclophane, which is structurally closely related to the Bergman-aromatization product of enediyne C-1027. We report an enantioselective synthesis of fijiolide A demonstrating the power of fully intermolecular ruthenium-catalyzed [2 + 2 + 2]-cyclotrimerizations with three different alkynes to assemble the heavily substituted central arene core. The characteristic strained [2.6]paracyclophane structure is accessed by a templated atropselective macroetherification reaction.

中文翻译：

通过 Atropselective Paracyclophane 形成合成斐济内酯 A

Fijiolide A 是一种从海洋来源的放线菌中分离出来的次级代谢物，对 TNF-α 诱导的 NFκB 激活具有抑制活性，NFκB 是一种重要的转录因子，是治疗不同癌症和炎症相关疾病的潜在靶点。Fijiolide A 是一种糖基化复合物对环芳烷，在结构上与烯二炔 C-1027 的伯格曼芳香化产物密切相关。我们报告了 fijiolide A 的对映选择性合成，展示了完全分子间钌催化的 [2 + 2 + 2]-环三聚与三种不同的炔烃以组装重取代的中心芳烃核心的能力。特征应变 [2.6] 对环芳烷结构可通过模板化的 atropselective 宏醚化反应获得。

更新日期：2015-08-27

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