Expeditious Synthesis of Vialinin B, an Extremely Potent Inhibitor of TNF-α Production

A first total synthesis of vialinin B, a powerful inhibitor (IC50 20 pM) of TNF-α 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 phenylacetyl...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2009-11, Vol.11 (21), p.5074-5077
Main Authors: Ye, Yue Qi, Koshino, Hiroyuki, Onose, Jun-ichi, Yoshikawa, Kunie, Abe, Naoki, Takahashi, Shunya
Format: Article
Language:English
Subjects:
Benzofurans - chemical synthesis
Benzofurans - chemistry
Catalysis
Molecular Structure
Phenylacetates - chemical synthesis
Phenylacetates - chemistry
Stereoisomerism
Tumor Necrosis Factor-alpha - antagonists & inhibitors
Tumor Necrosis Factor-alpha - biosynthesis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A first total synthesis of vialinin B, a powerful inhibitor (IC50 20 pM) of TNF-α 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9020833