Total Synthesis and Detection of the Bilirubin Oxidation Product (Z)-2-(3-Ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide (Z-BOX A)

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• 作者：Maurice Klopfleisch ; Raphael A. Seidel ; Helmar G枚rls ; Hannes Richter ; Rainer Beckert ; Wolfgang Imhof ; Markus Reiher ; Georg Pohnert ; Matthias Westerhausen
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：September 6, 2013
• 年：2013
• 卷：15
• 期：17
• 页码：4608-4611
• 全文大小：230K
• 年卷期：v.15,no.17(September 6, 2013)
• ISSN：1523-7052

文摘

The selective total synthesis of the pure Z-isomer of BOX A (8a), a product of oxidative heme degradation with significant physiological impact, was achieved in four to six steps starting from 3-bromo-4-methylfuran-2,5-dione (1). Z-BOX A forms a strong hydrogen bridge framework in the crystalline state. LC-MS techniques allow identification and characterization of isomeric forms of BOX A.