F. Hoper et Fp. Montforts, A SIMPLE SYNTHESIS OF FUNCTIONALIZED RAC-CHLORINS VIA ALLYLBORATION OF PORPHYRIN ALDEHYDES, Liebigs Annalen, (6), 1995, pp. 1033-1038
Chlorins rac-17a, b which bear terminally hydroxy-substituted butyl si
de chains were synthesized by allylboration and Claisen rearrangement
from readily accessible formylporphyrins 5 and 6. The hydroxyalkyl sid
e chain and the photophysical properties of the chlorins rac-17a, b sh
ould open a broad access to chlorins suitable for photodynamic therapy
having different residues attached to the hydroxy function. The repor
ted synthetic pathway also should be useful for the synthesis of natur
ally occurring hydroporphyrins containing geminally dialkylated struct
ural parts and a propionic acid residue on the saturated pyrrole ring.