Transformation of chlorins into bile pigment analogues
Treatment of trans-octaethylchlorin (1) with one equivalent of thallium(III) trifluoroacetate affords the corresponding aquo-hydroxide chelate (2) after chromatography on deactivated alumina; with four equivalents of the reagent, the ring opened dihydrobiliverdin (4) is obtained. When zinc trans-octaethylchlorin is treated with one equivalent of thallium(III) trifluoroacetate, the zinc meso-trifluoroacetoxy-trans-octaethylchlorin (12) is produced: hydrolysis of the trifluoroacetoxy-function in (12) in the presence of oxygen furnishes the dihydrobiliverdin (4) in high yield.
Publication Source (Journal or Book title)
Journal of the Chemical Society, Perkin Transactions 1
Cavaleiro, J., & Smith, K. (1973). Transformation of chlorins into bile pigment analogues. Journal of the Chemical Society, Perkin Transactions 1, 2149-2155. https://doi.org/10.1039/p19730002149