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Synthesis 2000; 2000(13): 1835-1838
DOI: 10.1055/s-2000-8238
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One-Step Conversion of 9-Methyl to 9-Formyldipyrrinones

Pavel Bobál* , David A. Lightner
  • *Department of Chemistry, University of Nevada, Reno, NV 89557, USA; Fax: +1(775)7 84 69 04; E-mail: lightner@scs.unr.edu
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Publikationsdatum:
31. Dezember 2000 (online)

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9-Formyldipyrrinones may be prepared on a synthetically useful scale in 80-90% yield by oxidation of 9-methyldipyrrinones with 2 equivalents of DDQ in TFA at -78°C. Whereas reaction at higher temperatures allows oxidative coupling to predominate, forming biliverdins as the major product, at low temperatures and under controlled conditions verdin formation becomes only a minor pathway.

oxidations - heterocycles - pyrroles - aldehydes