Ye Yue Qi, Koshino Hiroyuki, Onose Jun-ichi, Yoshikawa Kunie, Abe Naoki, Takahashi Shunya
RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan.
Org Lett. 2007 Oct 11;9(21):4131-4. doi: 10.1021/ol701590b. Epub 2007 Sep 12.
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.
紫铆因A是一种强大的肿瘤坏死因子-α产生抑制剂（IC50为90皮摩尔），由芝麻酚经11步合成，总产率为28%。关键反应包括富电子芳基三氟甲磺酸酯与苯硼酸的双铃木偶联反应以及双甲氧基甲基醚的氧化脱保护反应。此外，相关的合成研究还表明有必要对紫铆因A的位置异构体甘巴菌素C进行结构修正。
