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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)

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.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0003-7592-4 Version Permalink: https://hdl.handle.net/21.11116/0000-0009-3BB0-E
Genre: Journal Article

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EXT611.pdf (Publisher version), 333KB
 
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EXT611s2.pdf (Supplementary material), 4MB
 
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 Creators:
Klopfleisch, Maurice, Author
Seidel, Raphael A., Author
Goerls, Helmar, Author
Richter, Hannes, Author
Beckert, Rainer, Author
Imhof, Wolfgang, Author
Reiher, Markus, Author
Pohnert, Georg1, Author           
Westerhausen, Matthias, Author
Affiliations:
1External Organizations, ou_persistent22              

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Free keywords: REGIOSELECTIVE NUCLEOPHILIC ADDITIONS; SUBSTITUTED MALEIC ANHYDRIDES; CEREBRAL VASOSPASM; SUBARACHNOID HEMORRHAGE; 4-YLIDENEBUTENOLIDES; HEME; CHANNELSChemistry;
 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.

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Language(s): eng - English
 Dates: 2013
 Publication Status: Issued
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1021/ol402221b
Other: EXT611
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Title: Organic Letters
  Other : Org. Lett.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 15 (17) Sequence Number: - Start / End Page: 4608 - 4611 Identifier: ISSN: 1523-7060
CoNE: https://pure.mpg.de/cone/journals/resource/954925626338