Synthesis of models of metabolites: Oxidation of variously substituted chromenes including acronycine, by a porphyrin catalytic system

✍ Scribed by Bernardin Akagah; François Estour; Philippe Vérité; Elisabeth Seguin; Olivier Lafont; François Tillequin

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2005
• Tongue: English
• Weight: 124 KB
• Volume: 42
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570420704

✦ Synopsis

The influence of chemical neighbouring on oxidation of substituted 2,2-dimethylchromenes derivatives 5-8 by a biomimetic catalytic system was first studied. It was then applied to acronycine an anti-cancer drug in order to obtain in one single step oxidized products resulting from the reactivity of the 1,2-double bond in the pyranic D-ring. These 2,2-dimethylchromenes constitute the structural moiety responsible for the activity of acronycine. This oxidation showed the sensitivity of the ethylenic bond, leading to the formation of the corresponding epoxides, diols and/or ketoalcohol. In the case of 5-dimethylamino-2,2-dimethylchromene 8, the double bond was not sensitive to oxidation, but the N-methyl groups reacted to lead to the formamide derivative 16 and an imino-alcohol 17. This methodology applied to acronycine molecule 1, allowed to obtain in one step, two oxidized compounds, a trans-diol 3 and a ketoalcohol 4 under preparative conditions.