The Decomposition of cis-Fused Cyclopenteno-1,2,4-Trioxanes induced by Ferrous Salts and some oxophilic reagents

✍ Scribed by Charles W. Jefford; France Favarger; Maria Da Graça H. Vicente; Yvan Jacquier

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: German
• Weight: 456 KB
• Volume: 78
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19950780216

✦ Synopsis

proteolysis of ingested hemoglobin, is toxic to the parasite, but is normally removed by enzyme-catalyzed oxidative polymerization to hemozoin [3]. We speculated that 1 and 2 could interrupt this detoxification process by transferring an 0-atom to heme to create an iron-oxene intermediate or oxyheme which subsequently disables the parasite (Scheme I ). The complement of this process would be the formation of tihe 1,3-dioxolanes 3 and 4, respectively. In an attempt to evaluate 1,2,4-trioxanes as 0-atom transfer agents, we ') All products are racernic mixtures, but for the sake of clarity only one enantiomer is shown in the schemes ' )

Artemisinin (Z), on treatment with powdered Zn in AcOH, gives 4 exclusively (unpublished)