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Au-Catalyzed 1,3-Acyloxy Migration/Cyclization Cascade: A Direct Strategy toward the Synthesis of Functionalized Abietane-Type Diterpenes
CCS Chemistry ( IF 9.4 ) Pub Date : 2020-12-30 , DOI: 10.31635/ccschem.020.202000582
Tian-Lu Zheng 1 , Si-Zhan Liu 1 , Chen-Yu Huo 1 , Jing Li 1 , Bo-Wen Wang 1 , Da-Ping Jin 1 , Fu Cheng 1 , Xiao-Ming Chen 1 , Xiao-Ming Zhang 1 , Xue-Tao Xu 2 , Shao-Hua Wang 1
Affiliation  

A direct strategy toward the synthesis of functionalized abietane-type diterpenes and related polycyclic molecules was developed through an Au-catalyzed 1,3-acyloxy migration/cyclization/electrophilic aromatic substitution cascade. Unlike the known polyene-type cyclization strategies for the construction of abietane-type diterpene skeletons, propargylic ester groups were used for the cyclization process, which can readily lead to the key skeleton with C2 and C3 functionalization. As a demonstration of the potential application of this tandem reaction, a collective total synthesis of (±)-2-ketoferruginol, (±)-fleuryinol B, (±)-salviol, (±)-2β-acetoxyferruginol, and (±)-2β-acetoxysugiyl methyl ether was achieved. Among these molecules, (±)-fleuryinol B and (±)-2β-acetoxyferruginol were synthesized for the first time.



中文翻译:

Au催化的1,3-酰氧基迁移/环化级联:合成功能化的Abietane型二萜的直接策略。

通过Au催化的1,3-酰氧基迁移/环化/亲电子芳族取代级联反应,开发了一种直接合成官能化枞烷型二萜和相关多环分子的策略。不同于已知的多烯型环戊二烯骨架结构的环化策略,炔丙基酯基团用于环化过程,可以容易地导致关键骨架具有C2和C3官能化。为了证明该串联反应的潜在用途,共合成了(±)-2-酮基铁血红素醇,(±)-荧光白血球醇B,(±)-唾液醇,(±)-2β-乙酰氧基铁血红素醇和(±)获得了-2β-乙酰氧基苏糖基甲基醚。在这些分子中,首次合成了(±)-荧光白蛋白B和(±)-2β-乙酰氧基铁蛋白醇。

更新日期:2020-12-31
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