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  • Title: Expeditious synthesis of vialinin B, an extremely potent inhibitor of TNF-alpha production.
    Author: Ye YQ, Koshino H, Onose J, Yoshikawa K, Abe N, Takahashi S.
    Journal: Org Lett; 2009 Nov 05; 11(21):5074-7. PubMed ID: 19803477.
    Abstract:
    A first total synthesis of vialinin B, a powerful inhibitor (IC(50) 20 pM) of TNF-alpha production, is described. The key reactions include a double Suzuki-Miyaura coupling of electron-rich aryl bromide with a couple of phenylboronic acids, a Cu-mediated Ullmann reaction, and a LHMDS-promoted phenylacetylation. This synthesis proceeded in 11 steps with 18% overall yield from a known sesamol derivative.
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