Abstract
The esters of xanthobilirubic acid ( XBR) with rac -(±)-, ( R )-(+)-, and ( S )-(−)-alpha-methylbenzyl alcohol ( 1, 2 and 3 respectively), with rac -(±)-, ( R )-(+)-, and ( S )-(−)- sec -butyl alcohol ( 4, 5 and 6 respectively), with rac -(±)-, ( R )-(+)-, and ( S )-(−)-2-octanol ( 7, 8 and 9 respectively) have been synthesized in good to excellent yields using as condensing agent the mixture dicyclohexylcarbodiimide/ dimethylaminopyridine w(DCCI/ DMAP). These esters are models for the study of exciton coupling in hydrogen-bonded dimers. The esters of XBR with monomethoxypolyethyleneglycol (MPEG) of FW= 1900, and with polyethyleneglycol (PEG) of FW= 2000 ( 10 and 11 respectively) have been quantitatively prepared by the same procedure. These water-soluble dipyrrinone esters are models for the study of Z ∡ E photoisomerization in rats. Attempts to extrapolate the procedure to the synthesis of the same esters of bilirubin ( BR) have always led to difficult-to-separate mixtures of products.
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