First Total Synthesis of Vialinin A, a Novel and Extremely Potent Inhibitor of TNF-α Production

Vialinin A, a powerful inhibitor (IC50 90 pM) of TNF-α 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, t...

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Bibliographic Details
Published in:Organic letters 2007-10, Vol.9 (21), p.4131-4134
Main Authors: Ye, Yue Qi, Koshino, Hiroyuki, Onose, Jun-ichi, Yoshikawa, Kunie, Abe, Naoki, Takahashi, Shunya
Format: Article
Language:English
Subjects:
Biphenyl Compounds - chemistry
Molecular Structure
Stereoisomerism
Terphenyl Compounds - chemical synthesis
Terphenyl Compounds - chemistry
Terphenyl Compounds - pharmacology
Tumor Necrosis Factor-alpha - antagonists & inhibitors
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Summary:Vialinin A, a powerful inhibitor (IC50 90 pM) of TNF-α 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol701590b