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

M. Buccini, K.A. Punch, Belinda Kaskow, Gavin Flematti, Brian Skelton, Lawrence Abraham, Matthew Piggott

Research output: Contribution to journalArticle

16 Citations (Scopus)

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. This journal is © The Royal Society of Chemistry.
Original languageEnglish
Pages (from-to)1100-1113
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number7
DOIs
Publication statusPublished - 2014

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