Fr. Trull et al., A GENERALIZED-METHOD FOR SYNTHESIZING UNSYMMETRIC FROM SYMMETRICAL BILE-PIGMENTS, Synthetic communications, 23(19), 1993, pp. 2771-2783
Two general rules are proposed for synthesizing unsymmetric from symme
tric bile pigments based on a ''reverse scrambling'' strategy and pola
rity/acid-base properties of reactants and products, to facilitate sep
aration of the target unsymmetrical bilirubin, such as mesobilirubin-V
IIIalpha and others. By this method 17-desvinyl-17-ethyl-bilirubin-VII
Ialpha, mesobilirubin-VIIIalpha, 12-despropionic acid-12-ethyl-mesobil
irubin-XIIIalpha, 17-desvinyl-17-ethyl-bilirubin-XIIIalpha and 18-desv
inyl-18-ethyl-bilirubin-IXalpha are synthesized.