Total Synthesis of the Urobiliverdin and Coprobiliverdin Isomers

VALASINAS ALDONIA; SAMBROTTA LUIS; DIAZ LUIS E; FRYDMAN BENJAMIN

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; Año: 1986 p. 3001 - 3006

0022-3263

The total synthesis of the five urobiliverdin isomers which can be derived from the oxidation of uroheme I and uroheme I11 was achieved, as well as the synthesis of the five coprobiliverdin isomers which can be derived from the oxidation of coproheme I and coproheme 111. The biliverdins were obtained by oxidation of the corresponding 1,19-bis[ (tert-butyloxy)carbonyl]-b-bilenes. The latter were obtained by condensation of the appropriate 5´-[(tert-butylo~)carbonyl]-5-formyldipyrrylmethanews ith the a-unsubstituted 2 4( tert-butyloxy)carbonyl]dipyrrylmethanes. Urobiliverdin I was found to be identical with bactobilin, a bile pigment isolated from anaerobic microorganisms.