Chemistry Letters, Vol.49, No.3, 287-289, 2020
Synthesis of Sedimentary Porphyrin-like Chlorophyll-a Derivatives Lacking the 3-Substituent
Nickel methyl 3-devinyl-pyropheophorbide-a was unexpectedly synthesized by chemical modification of naturally occurring chlorophyll-a. The removal of the 3-substituents proceeded by heating in an acidic solution at 80 degrees C. 1-Hydroxyethyl, vinyl, acetyl, and ethynyl groups at the 3-position were eliminated under mild conditions, but the 3-ethyl, hydroxymethyl, and formyl groups could not be done. This 3-unsubstituted compound, obtained in up to 31% yield, was similar to sedimentary porphyrins. Therefore, this work would advance understanding of the biomarker identities in geological samples.