Synlett 1994; 1994(10): 777-785
DOI: 10.1055/s-1994-23004
account
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthetic Strategies for Understanding Bilirubin Stereochemistry

Stefan E. Boiadjiev* , David A. Lightner
  • *Department of Chemistry, University of Nevada, Reno, Nevada 89557-0020, USA
Further Information

Publication History

Publication Date:
22 March 2002 (online)

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