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Synlett 1994; 1994(10): 777-785
DOI: 10.1055/s-1994-23004
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Synthetic Strategies for Understanding Bilirubin Stereochemistry

Stefan E. Boiadjiev* , David A. Lightner
  • *Department of Chemistry, University of Nevada, Reno, Nevada 89557-0020, USA
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Publication Date:
22 March 2002 (online)

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Synthetic approaches toward model tetrapyrrolic bilirubin-like analogs are described. The consequences of judiciously targeted remote variations of primary chemical structure on the three-dimensional shape of bilirubin analogs are discussed. 1. Introduction 2. Structural Features of Bilirubin 3. Synthons for Bilirubin Analogs 4. Oxidative Coupling of Dipyrrinones to Give Symmetric Rubins 5. Bilirubin Analogs via Scrambling of Dipyrrinone Subunits, A Route to Unsymmetric Rubins (Mesobilirubin-VIIIα) 6. Synthesis of 10,10-Dimethyl Bilirubin Analogs 7. Synthesis of Carboxyrubin 8. Conclusions

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