Issue 7, 2014

Ethynylbenzenoid metabolites of Antrodia camphorata: synthesis and inhibition of TNF expression

Abstract

An improved synthesis of the anti-inflammatory natural product antrocamphin A (2), involving a key Castro–Stephens reaction, is presented, along with the first total synthesis of its congener antrocamphin B (3). Approaches towards the more complex co-metabolite antrodioxolanone (4) were unsuccessful, but a samarium diiodide-mediated pinacol coupling of antrocamphin B did provide the chiral epimers (51). Antrocamphin A (2) inhibits Tumour Necrosis Factor (TNF) reporter gene expression, but its development as an anti-inflammatory agent may be limited by cytotoxicity.

Graphical abstract: Ethynylbenzenoid metabolites of Antrodia camphorata: synthesis and inhibition of TNF expression

Supplementary files

Article information

Article type
Paper
Submitted
22 Nov 2013
Accepted
18 Dec 2013
First published
19 Dec 2013
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2014,12, 1100-1113

Author version available

Ethynylbenzenoid metabolites of Antrodia camphorata: synthesis and inhibition of TNF expression

M. Buccini, K. A. Punch, B. Kaskow, G. R. Flematti, B. W. Skelton, L. J. Abraham and M. J. Piggott, Org. Biomol. Chem., 2014, 12, 1100 DOI: 10.1039/C3OB42333F

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