Total synthesis and detection of the Bilirubin oxidation product 
(Z)-2-(3-Ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanami de 
(Z-BOX A)

Klopfleisch, Maurice; Seidel, Raphael A.; Goerls, Helmar; Richter, Hannes; Beckert, Rainer; Imhof, Wolfgang; Reiher, Markus; Pohnert, Georg; Westerhausen, Matthias

doi:10.1021/ol402221b

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Total synthesis and detection of the Bilirubin oxidation product (Z)-2-(3-Ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanami de (Z-BOX A)

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Klopfleisch, M., Seidel, R. A., Goerls, H., Richter, H., Beckert, R., Imhof, W., et al. (2013). Total synthesis and detection of the Bilirubin oxidation product (Z)-2-(3-Ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanami de (Z-BOX A). Organic Letters, 15(17), 4608-4611. doi:10.1021/ol402221b.

Cite as: https://hdl.handle.net/21.11116/0000-0003-7592-4

Abstract

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.