Syntheses of chiral fluorine analogs of hematoporphyrin

Four chiral fluorine analogs of hematoporphyrin, (R,R)-, (R,S)-, (S,R)-, and (S,S)-3,8-bis(2,2,2-trifluoro-1-hydroxyethyl)deuteroporphyrins, were synthesized starting from pyrroles with a chiral 2,2,2-trifluoro-1-hydroxyethyl (TFHE) group. This chiral TFHE group was obtained by asymmetric reduction of a trifluoroacetyl group. Among these chiral analogs of hematoporphyrin, the (S,S)-isomer showed higher affinity for cancer cells than other stereoisomers.