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 language | English |
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Pages (from-to) | 1100-1113 |
Journal | Organic and Biomolecular Chemistry |
Volume | 12 |
Issue number | 7 |
DOIs | |
Publication status | Published - 2014 |