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First total synthesis of vialinin A, a novel and extremely potent inhibitor of TNF-alpha production.
Organic Letters ( IF 5.2 ) Pub Date : 2007 Oct 11 , DOI: 10.1021/ol701590b
Yue Qi Ye 1 , Hiroyuki Koshino 1 , Jun-ichi Onose 1 , Kunie Yoshikawa 1 , Naoki Abe 1 , Shunya Takahashi 1
Affiliation  

Vialinin A, a powerful inhibitor (IC50 90 pM) of TNF-alpha production, was synthesized from sesamol in 11 steps with 28% overall yield. The key reactions include a double Suzuki coupling of electron-rich aryl triflate with phenylboronic acid and an oxidative deprotection of bis-MOM ether. In addition, the related synthetic studies also suggest the necessity for structural revision of ganbajunin C, a positional isomer of vialinin A.

中文翻译:

Vialinin A的第一个全合成,这是一种新型且非常有效的TNF-α抑制剂。

从芝麻素中分11步合成了功能强大的TNF-α抑制剂(IC50 90 pM)Vialinin A,总产率为28%。关键反应包括富电子的三氟甲磺酸芳基酯与苯基硼酸的双Suzuki偶联和bis-MOM醚的氧化脱保护。此外,相关的合成研究还表明,对甘菊碱C(一种小林蛋白A的位置异构体)进行结构修订的必要性。
更新日期:2017-01-31
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